Design and synthesis of (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid

Bhaskar C. Das; George W. Kabalka

doi:10.1016/j.tetlet.2008.05.136

Design and synthesis of (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid

Bhaskar C. Das
, George W. Kabalka

Pharmaceutical Sciences

University of Tennessee

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

(E)-4-((3-Ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid, 6, was synthesized in 87% starting from β-cyclocitral. The target compound 6 was synthesized starting from 1 via a Grignard reaction to form alcohol 2. Compound 2 was converted to Wittig salt 3 by treatment with aldehyde 4 in butyllithium and hexane at -78 °C to form ester 5. Ester 5 was saponified and, following acidification, acid 6 was isolated as white solid yield 87%.

Original language	English
Pages (from-to)	4695-4696
Number of pages	2
Journal	Tetrahedron Letters
Volume	49
Issue number	32
DOIs	https://doi.org/10.1016/j.tetlet.2008.05.136
State	Published - Aug 4 2008

Keywords

1,4 Diene and Wittig reaction
Peptidomimetics
Retinoids

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10.1016/j.tetlet.2008.05.136

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title = "Design and synthesis of (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid",

abstract = "(E)-4-((3-Ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid, 6, was synthesized in 87\% starting from β-cyclocitral. The target compound 6 was synthesized starting from 1 via a Grignard reaction to form alcohol 2. Compound 2 was converted to Wittig salt 3 by treatment with aldehyde 4 in butyllithium and hexane at -78 °C to form ester 5. Ester 5 was saponified and, following acidification, acid 6 was isolated as white solid yield 87\%.",

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author = "Das, \{Bhaskar C.\} and Kabalka, \{George W.\}",

year = "2008",

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doi = "10.1016/j.tetlet.2008.05.136",

language = "English",

volume = "49",

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journal = "Tetrahedron Letters",

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T1 - Design and synthesis of (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid

AU - Das, Bhaskar C.

AU - Kabalka, George W.

PY - 2008/8/4

Y1 - 2008/8/4

N2 - (E)-4-((3-Ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid, 6, was synthesized in 87% starting from β-cyclocitral. The target compound 6 was synthesized starting from 1 via a Grignard reaction to form alcohol 2. Compound 2 was converted to Wittig salt 3 by treatment with aldehyde 4 in butyllithium and hexane at -78 °C to form ester 5. Ester 5 was saponified and, following acidification, acid 6 was isolated as white solid yield 87%.

AB - (E)-4-((3-Ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid, 6, was synthesized in 87% starting from β-cyclocitral. The target compound 6 was synthesized starting from 1 via a Grignard reaction to form alcohol 2. Compound 2 was converted to Wittig salt 3 by treatment with aldehyde 4 in butyllithium and hexane at -78 °C to form ester 5. Ester 5 was saponified and, following acidification, acid 6 was isolated as white solid yield 87%.

KW - 1,4 Diene and Wittig reaction

KW - Peptidomimetics

KW - Retinoids

UR - https://www.scopus.com/pages/publications/45649083528

U2 - 10.1016/j.tetlet.2008.05.136

DO - 10.1016/j.tetlet.2008.05.136

M3 - Article

AN - SCOPUS:45649083528

SN - 0040-4039

VL - 49

SP - 4695

EP - 4696

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

Design and synthesis of (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid

Abstract

Keywords

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