N,N-diethyl-4-formylbenzamide → 4-(N,N-diethylcarbamoyl)benzhydryl alcohol

HRID 538288Notes

Reaction equation

[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:9]([C:11]1[CH:23]=[CH:22][C:14]([C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1)=[O:10]>O1CCCC1>[CH2:20]([N:17]([CH2:18][CH3:19])[C:15]([C:14]1[CH:22]=[CH:23][C:11]([CH:9]([OH:10])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:12][CH:13]=1)=[O:16])[CH3:21]

Participants

Conditions

Temperature: -78 °C

Procedure

Phenylmagnesium bromide (1.0 M solution in tetrahydrofuran, 235 mL, 235 mmol) was slowly added to a flask containing a cold (−78° C.) solution of 4-formyl-N,N-diethylbenzamide (48.18 g, 235 mmol) in 500 mL of dry tetrahydrofuran under nitrogen. The transfer rate was monitored to maintain reaction temperature below −70° C. The reaction was stirred for another 45 minutes at −78° C. and then quenched with 45 mL of saturated aqueous ammonium chloride. After warming to room temperature, the mixture was diluted with 900 mL of diethyl ether and washed with 900 mL of water followed by 230 mL of saturated sodium chloride. The ethereal solution was dried over sodium sulfate and the solvent removed to give crude 4-(N,N-diethylcarbamoyl)benzhydryl alcohol as a light yellow oil. Crude yield was ˜92%.

Workup

temperatureto maintain
customreaction temperature below −70° C
customquenched with 45 mL of saturated aqueous ammonium chloride
temperatureAfter warming to room temperature
additionthe mixture was diluted with 900 mL of diethyl ether
washwashed with 900 mL of water
dry with materialThe ethereal solution was dried over sodium sulfate
customthe solvent removed

Sources & evidence

ORD record: ord-c5026d84660d4697846fe207679b8ea8
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865721B2

Reaction notes

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