Acetonitrile → HCID 19107597, compound
Reaction equation
[C:1](#[N:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].[CH3:12][O:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[O:19])=[CH:16][CH:15]=1>C1COCC1>[OH:19][C:18]([C:17]1[CH:28]=[CH:29][C:14]([O:13][CH3:12])=[CH:15][CH:16]=1)([C:20]1[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[CH2:2][C:1]#[N:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Acetonitrile (3.2 ml, 0.058 mol) was added dropwise to a solution of lithium diisopropylamide (1.5M in THF, 36.7 ml, 0.055 mol) stirred at -78° C. under argon. After 5 min. a solution of 4,4'-dimethoxybenzophenone (10.0 g, 0.048 mol) in dry THF (130 ml) was added slowly. The mixture was allowed to warm up to -35° C. and after 20 min. was quenched by the cautious dropwise addition of a solution of acetic acid (3.0 g) in water (6 ml). Brine (50 ml) was added, the organic layer separated washed with brine (50 ml) and the combined aqueous phases were extracted with DCM (2×50 ml). The combined organics were dried over anhydrous magnesium sulphate, filtered and concentrated. The residue was crystallised from ethyl acetate to give 3-hydroxy-3,3-di(4-methoxyphenyl)propanenitrile (10.12 g, 85%) as a white crystalline solid.
Workup
- temperatureto warm up to -35° C. and after 20 min.
- customwas quenched by the cautious dropwise addition of a solution of acetic acid (3.0 g) in water (6 ml)
- additionBrine (50 ml) was added
- customthe organic layer separated
- washwashed with brine (50 ml)
- extractionthe combined aqueous phases were extracted with DCM (2×50 ml)
- dry with materialThe combined organics were dried over anhydrous magnesium sulphate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was crystallised from ethyl acetate
Sources & evidence
- ORD record
- ord-6ffe97fee8c74404b285ff136405d406
- Source dataset
- uspto-grants-1993_01
- Patent number
- US05180723
Reaction notes
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