Acetonitrile → HCID 19107597, compound

HRID 1197644Notes

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

Conditions

Temperature: -78 °C

Procedure

Acetonitrile (3.2 ml, 0.058 mol) was added dropwise to a solution of lithium diisopropylamide (1.5 M 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 crystalised 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 crystalised from ethyl acetate

Sources & evidence

ORD record: ord-cf480a55a5414d158a29f7b18f709f53
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05276153

Reaction notes

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