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

HRID 496189

Reaction equation

HRID 496189 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  1. customkept at ambient temperature by a water bath

Sources & evidence

ORD record
ord-bfa86f5257fc4cc08e7b8fb76e4ff145
Source dataset
uspto-grants-2005_09
Patent number
US06943188B2

Linked notes

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