2-[(4-Chlorophenyl)carbonyl]cyclopropanecarbonitrile → 2-[1-(4-Chlorophenyl)-1-hydroxyethyl]cyclopropanecarbonitrile
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:12][CH:11]2[C:13]#[N:14])=[O:9])=[CH:4][CH:3]=1.[CH3:15][Mg]Br>C(OCC)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:10]2[CH2:12][CH:11]2[C:13]#[N:14])([OH:9])[CH3:15])=[CH:6][CH:7]=1Participants
4
Procedure
714 mg of the compound from Example 74A with a purity of 54% (1.89 mmol) were introduced into 7 ml of diethyl ether at RT, 0.94 ml (2.83 mmol) of a 3N solution of methylmagnesium bromide in diethyl ether was added, and the mixture was stirred at RT overnight. The reaction mixture was added to a saturated, ice-cold aqueous ammonium chloride solution, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile-water gradient) to result in 257 mg (55% of theory) of the title compound.