2-Formyl-3-[(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene → 4-[(E)-2-(5,5,8,8-tetramethyl-3-thiophen-2ylmethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoic acid

HRID 1836890Notes

Reaction equation

C(C1C(CC2SC=CC=2)=CC2C(C)(C)CCC(C)(C)C=2C=1)=O.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[CH2:28][C:29]1[C:30](/[CH:43]=[CH:44]/[C:45]2[CH:55]=[CH:54][C:48]([C:49]([O:51]CC)=[O:50])=[CH:47][CH:46]=2)=[CH:31][C:32]2[C:33]([CH3:42])([CH3:41])[CH2:34][CH2:35][C:36]([CH3:40])([CH3:39])[C:37]=2[CH:38]=1>>[CH3:39][C:36]1([CH3:40])[CH2:35][CH2:34][C:33]([CH3:41])([CH3:42])[C:32]2[CH:31]=[C:30](/[CH:43]=[CH:44]/[C:45]3[CH:46]=[CH:47][C:48]([C:49]([OH:51])=[O:50])=[CH:54][CH:55]=3)[C:29]([CH2:28][C:24]3[S:23][CH:27]=[CH:26][CH:25]=3)=[CH:38][C:37]1=2

Participants

Reactant 2

HCID 234989152-Formyl-3-[(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene

HCID 86585387ethyl (E)-4-{2-[3-((thiophene-2-yl)methyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]vinyl}benzoate

Product 1

HCID 101135414-[(E)-2-(5,5,8,8-tetramethyl-3-thiophen-2ylmethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoic acidYield 63.3%

Procedure

Horner-Emmons olefination (following the procedure of Example) of 2-formyl-3-[(thiophene-2-yl)methyl]-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (94 mg, 0.3 mmol) followed by ester hydrolysis (following the procedure of Example) of ethyl (E)-4-{2-[3-((thiophene-2-yl)methyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl]vinyl}benzoate (53 mg, 0.11 mmol) provides 4-[(E)-2-(5,5,8,8-tetramethyl-3-thiophen-2ylmethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoic acid (30 mg, 63%) as a white crystalline solid 44 (m.p. 229.1-229.6° C.).

Sources & evidence

ORD record: ord-91b7dbfef13e46ccbd955abc21cef639
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777418B2

Reaction notes

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