Triphenylphosphine → methyl (R)-7-(4-fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoate

HRID 37720

반응식

HRID 37720 반응식
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].[F:11][C:12]1[CH:17]=[CH:16][C:15]([C@@H:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:14][CH:13]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>ClCCCl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]([C:4]2[C:5]([CH3:9])=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[C:3]=2[OH:10])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 127692,3,5-TrimethylphenolHCID 5462977Diethyl azodicarboxylateHCID 10562892methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate

생성물 1

HCID 10714337methyl (R)-7-(4-fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoate수율 33.6%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

실험 절차

To a solution of 2,3,5-trimethylphenol (0.80 g, 5.9 mmol), methyl (S)-7-(4-fluorophenyl)-7-hydroxyheptanoate (0.30 g, 1.2 mmol) and triphenylphosphine (0.46 g, 1.8 mmol) in 1,2-dichloroethane (20 ml) was added at 10° C. a solution of 95% DEAD (0.54 ml) in 1,2-dichloroethane (5 ml) taking 30 minutes. The mixture was stirred for one hour at the same temperature range, then the solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography to give 0.15 g of methyl (R)-7-(4-fluorophenyl)-7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoate.

후처리

  1. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-9323b5e843c14389855dc61cea00165b
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420363

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