N-(2-hydroxy-2-phenylethyl)pent-4-ynamide → Pent-4-ynoic acid (2-oxo-2-phenyl-ethyl)-amide
Reaction equation
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][NH:4][C:5](=[O:10])[CH2:6][CH2:7][C:8]#[CH:9].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[O:1]=[C:2]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:3][NH:4][C:5](=[O:10])[CH2:6][CH2:7][C:8]#[CH:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
169 mg (0.78 mmol) of N-(2-hydroxy-2-phenylethyl)pent-4-ynamide in DCM (1 mL) were added to a solution of PCC (326 mg, 1.48 mmol) in DCM (4 mL). The reaction mixture was stirred for 4 hours at room temperature, dissolved in DCM and then quenched with NaOH 1N. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated to yield 160 mg (0.74 mmol, 95%) of pent-4-ynoic acid (2-oxo-2-phenyl-ethyl)-amide as a yellow solid.