N-Methoxy-N-methylacetamide → 2-(4-Acetylphenyl)-2-methylpropanenitrile

HRID 419942Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:21](=[O:23])[CH3:22]>C1COCC1>[C:21]([C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:12])([CH3:11])[C:9]#[N:10])=[CH:4][CH:3]=1)(=[O:23])[CH3:22]

Participants

Conditions

Temperature: -100 °C

Procedure

2-(4-bromophenyl)-2-methylpropanenitrile (1 g, 4.46 mmol) is dissolved in anhydrous THF (75 ml) the solution is cooled down to −100° C. with a diethyl ether-liquid nitrogen bath, n-butyl lithium 2M in c-hexane (4.0 ml, 8.0 mmol) is added and this reaction mixture stirred for 10 min., then N-methoxy-N-methyl acetamide (1.6 g, 15.6 mmol) is added and the reaction is then left to slowly warm-up to room temperature. After work-up (washing with acidic brine) and concentration the crude mixture is purified on silica gel using a 0 to 50% ethyl acetate in hexane gradient, to give the desired compound (660 mg, 78%) as a clear oil.

Workup

waitthe reaction is then left
temperatureto slowly warm-up to room temperature
washAfter work-up (washing with acidic brine) and concentration the crude mixture
customis purified on silica gel using a 0 to 50% ethyl acetate in hexane gradient

Sources & evidence

ORD record: ord-0b06eb5bd69d403db9ed2fc14906cc56
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093402B2

Reaction notes

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