Synthesis of fluorinated analogs of geraniol

…, PL Wiggins, TL Plummer

Index: Poulter, C. Dale; Wiggins, Paul L.; Plummer, Thomas L. Journal of Organic Chemistry, 1981 , vol. 46, # 8 p. 1532 - 1538

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Citation Number: 56

Abstract

Results and Discussion 3-(Fluoromethyl) geraniol (4). A stereoselective synthesis of 3- (fluoromethy1) geraniol (4) is presented in Scheme I. The key reaction is the conjugate addition of the 4-methylpent-3-en-1-yl moiety (C6HI1) to acetylenic ester 1. This step establishes the correct stereochemistry

 Related Synthetic Route
acetic acid,2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

76480-90-5

acetic acid,2-(...

~53%

acetic acid,3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

76481-05-5

acetic acid,3-(...

5-Bromo-2-methyl-2-pentene Structure

2270-59-9

5-Bromo-2-methy...

~%

acetic acid,3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

76481-05-5

acetic acid,3-(...

N/A Structure

76481-04-4

N/A

~%

acetic acid,3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

76481-05-5

acetic acid,3-(...

(Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dien-1-yl acetate Structure

76480-88-1

(Z)-3-[[(1'-oxa...

~%

acetic acid,3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

76481-05-5

acetic acid,3-(...

ethyl (Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dienoate Structure

76480-87-0

ethyl (Z)-3-[[(...

~%

acetic acid,3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

76481-05-5

acetic acid,3-(...

ethyl (Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dienoate Structure

76480-87-0

ethyl (Z)-3-[[(...

~62%

3-(4-methylpent-3-enyl)-2H-furan-5-one Structure

61315-75-1

3-(4-methylpent...

5-Bromo-2-methyl-2-pentene Structure

2270-59-9

5-Bromo-2-methy...

~%

3-(4-methylpent-3-enyl)-2H-furan-5-one Structure

61315-75-1

3-(4-methylpent...

acetic acid,3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

76481-05-5

acetic acid,3-(...

~83%

3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

76480-89-2

3-(fluoromethyl...

5-Bromo-2-methyl-2-pentene Structure

2270-59-9

5-Bromo-2-methy...

~%

3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

76480-89-2

3-(fluoromethyl...

acetic acid,2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

76480-90-5

acetic acid,2-(...

~%

3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

76480-89-2

3-(fluoromethyl...

N/A Structure

76481-04-4

N/A

~%

3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

76480-89-2

3-(fluoromethyl...

(Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dien-1-yl acetate Structure

76480-88-1

(Z)-3-[[(1'-oxa...

~%

3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

76480-89-2

3-(fluoromethyl...

ethyl (Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dienoate Structure

76480-87-0

ethyl (Z)-3-[[(...

~%

3-(fluoromethyl)-7-methylocta-2,6-dien-1-ol Structure

76480-89-2

3-(fluoromethyl...

5-Bromo-2-methyl-2-pentene Structure

2270-59-9

5-Bromo-2-methy...

~%

acetic acid,2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

76480-90-5

acetic acid,2-(...

N/A Structure

76481-04-4

N/A

~%

acetic acid,2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

76480-90-5

acetic acid,2-(...

ethyl (Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dienoate Structure

76480-87-0

ethyl (Z)-3-[[(...

~%

acetic acid,2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

76480-90-5

acetic acid,2-(...

(Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dien-1-yl acetate Structure

76480-88-1

(Z)-3-[[(1'-oxa...

~60%

2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

76480-92-7

2-(4-methylpent...

acetic acid,2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

76480-90-5

acetic acid,2-(...

(Z)-3-(acetoxymethyl)-7-methylocta-2,6-dien-1-ol Structure

76480-91-6

(Z)-3-(acetoxym...

(Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dien-1-yl acetate Structure

76480-88-1

(Z)-3-[[(1'-oxa...

~3%

2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

76480-92-7

2-(4-methylpent...

acetic acid,2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

76480-90-5

acetic acid,2-(...

(Z)-3-(acetoxymethyl)-7-methylocta-2,6-dien-1-ol Structure

76480-91-6

(Z)-3-(acetoxym...

N/A Structure

76481-04-4

N/A

~%

2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

76480-92-7

2-(4-methylpent...

ethyl (Z)-3-[[(1'-oxacyclohex-2'-yl)oxy]methyl]-7-methylocta-2,6-dienoate Structure

76480-87-0

ethyl (Z)-3-[[(...

~%

2-(4-methylpent-3-enyl)but-2-ene-1,4-diol Structure

76480-92-7

2-(4-methylpent...

2-Butynoic acid, 4-hydroxy-, ethyl ester Structure

31555-04-1

2-Butynoic acid...

~57%

ethyl 4-fluorobut-2-ynoate Structure

76480-93-8

ethyl 4-fluorob...

ethyl 4-(tetrahydro-2H-pyran-2-yloxy)but-2-ynoate Structure

31555-03-0

ethyl 4-(tetrah...

~%

ethyl 4-fluorobut-2-ynoate Structure

76480-93-8

ethyl 4-fluorob...


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