Ethyl Acetate → HCID 86660475, compound

HRID 41724

Reaction equation

[C:1](Cl)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:21]([O:25][C:26](=[O:52])/[CH:27]=[CH:28]/[C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[C:37]([C:42]34[CH2:51][CH:46]5[CH2:47][CH:48]([CH2:50][CH:44]([CH2:45]5)[CH2:43]3)[CH2:49]4)[CH:36]=2)=[CH:31][CH:30]=1)([CH3:24])([CH3:23])[CH3:22].CCOC(C)=O>N1C=CC=CC=1>[C:42]12([C:37]3[CH:36]=[C:35]([C:32]4[CH:33]=[CH:34][C:29]([CH:28]=[CH:27][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:52])=[CH:30][CH:31]=4)[CH:40]=[CH:39][C:38]=3[O:41][C:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[CH2:11][CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:43][CH:44]3[CH2:50][CH:48]([CH2:47][CH:46]([CH2:45]3)[CH2:51]1)[CH2:49]2

Participants

Conditions

Temperature: 50 °C

Procedure

Linoleoyl chloride (208 mg, 0.696 mmol) was added to a solution of (E)-3-(3′-adamantan-1-yl-4′-hydroxybiphenyl-4-yl)-acrylic acid tert-butyl ester (200 mg, 0.464 mmol) in pyridine (2.2 ml). The resulting mixture was heated to 50° C. for 1 h, and then stirred at RT overnight. After addition of EtOAc, the organic phase was washed twice with 1N HCl, water, dried over Na2SO4, filtered and removed under reduced pressure. (E)-Octadeca-9,12-dienoic acid 3-adamantan-1-yl-4′-(2-tert-butoxycarbonylvinyl)biphenyl-4-yl ester was obtained as a colourless oil after purification on silica gel (EtOAc/hexane 5:95) in 65% yield (210 mg).

Workup

washthe organic phase was washed twice with 1N HCl, water
dry with materialdried over Na2SO4
filtrationfiltered
customremoved under reduced pressure

Sources & evidence

ORD record: ord-470bff9b5847421b9928813953b96742
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530517B2

Linked notes

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