HCID 23498936, compound → HCID 10115506, compound

HRID 1836894Notes

Reaction equation

C(C1C(CC2C=CC(C)=CC=2)=CC2C(C)(C)CCC(C)(C)C=2C=1)=O.[CH3:25][C:26]1([CH3:60])[CH2:35][CH2:34][C:33]([CH3:37])([CH3:36])[C:32]2[CH:31]=[C:30](/[CH:38]=[CH:39]/[C:40]3[CH:50]=[CH:49][C:43]([C:44]([O:46]CC)=[O:45])=[CH:42][CH:41]=3)[C:29]([CH2:51][C:52]3[CH:57]=[CH:56][C:55]([F:58])=[CH:54][C:53]=3[F:59])=[CH:28][C:27]1=2>>[CH3:25][C:26]1([CH3:60])[CH2:35][CH2:34][C:33]([CH3:36])([CH3:37])[C:32]2[CH:31]=[C:30](/[CH:38]=[CH:39]/[C:40]3[CH:50]=[CH:49][C:43]([C:44]([OH:46])=[O:45])=[CH:42][CH:41]=3)[C:29]([CH2:51][C:52]3[CH:57]=[CH:56][C:55]([F:58])=[CH:54][C:53]=3[F:59])=[CH:28][C:27]1=2

Participants

Reactant 2

HCID 23498936HCID 23498936, compound

HCID 23498979HCID 23498979, compound

Product 1

HCID 10115506HCID 10115506, compoundYield 72%

Procedure

Horner-Emmons olefination (following the procedure of Example) of 2-formyl-3-(4-methylbenzyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (239 mg, 0.69 mmol) followed by ester hydrolysis (following the procedure of Example) of ethyl 4-{(E)-2-[5,5,8,8-tetramethyl-3-(2,4-difluorobenzyl)-5,6,7,8-tetrahydro-naphthalen-2-yl]vinyl}benzoate gave 4-{(E)-2-[5,5,8,8-tetramethyl-3-(2,4-difluorobenzyl)-5,6,7,8-tetrahydro-naphthalen-2-yl]vinyl}benzoic acid (230 mg, 72%) as a white crystalline solid (m.p. 204.3-205.7° C.) recrystallized from (CH2Cl2/hexane) 43.

Sources & evidence

ORD record: ord-ea1ae1f494694fe398a365adc4e21671
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777418B2

Reaction notes

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