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

HRID 965891Notes

Reaction equation

HRID 965891 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-d8e69c412bee41dbad9f1cdb3299855d
Source dataset
uspto-grants-2005_10
Patent number
US06951874B2

Reaction notes

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