Triphenylphosphine → N-[2-(2-cyclohexen-1-yloxy)phenyl]acetamide

HRID 496189

반응식

HRID 496189 반응식
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[C:8]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1O)(=[O:10])[CH3:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(=O)ON=NOC(=O)OCC)C>C1COCC1>[CH:1]1([O:7][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:8](=[O:10])[CH3:9])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 119722-AcetamidophenolHCID 131982-Cyclohexen-1-OLHCID 54051361Diethyl azodicarbonic acid

생성물 1

HCID 22313659N-[2-(2-cyclohexen-1-yloxy)phenyl]acetamide수율 19.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

2-Cyclohexenol (491 mg, 0.49 ml, 5.00 mmol, 1.0 equiv.), 2-acetamidophenol (756 mg, 5.00 mmol, 1.0 equiv.) and triphenylphosphine (1.44 g, 5.50 mmol, 1.1 equiv.) were dissolved in THF (10 ml) and kept at ambient temperature by a water bath. After dropwise addition of diethyl azodicarbonic acid (871 mg, 0.78 ml, 5.00 mmol, 1.0 equiv.), dissolved in THF (3 ml), the reaction mixture was stirred over night. Extractive work-up and flash chromatography on silica gel (heptane/tertbutyl(methyl)ether=1:1) afforded 224 mg (19%) the title compound as a yellow oil.

후처리

  1. customkept at ambient temperature by a water bath

출처 및 근거

ORD 기록
ord-bfa86f5257fc4cc08e7b8fb76e4ff145
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06943188B2

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