Benzyl Bromide → 3-benzyl-3-[(diphenylmethylene)amino]dihydrofuran-2(3H)-one

HRID 1160179Notes

Reaction equation

[C:1]1([C:7](=[N:14][CH:15]2[CH2:19][CH2:18][O:17][C:16]2=[O:20])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[CH2:31]([C:15]1([N:14]=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:19][CH2:18][O:17][C:16]1=[O:20])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-[(diphenylmethylene)amino]dihydrofuran-2(3H)-one (1 g, 3.8 mmol) in DMF (10 mL) cooled to 0° C. was added NaHMDS (4.7 mL, 4.7 mmol, 1M THF) via serynge slowly. The resulting bright orange solution was stirred at 0° C. for 2 min at which point benzyl bromide (0.47 mL, 4 mmol) was addedvia serynge. After 5 min stirring at 0° C., the reaction was quenched with water, extracted with EtOAc, washed with aqueous LiCl, dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography (90 g silica gel, 0 to 40% EtOAc in hexane) to give 3-benzyl-3-[(diphenylmethylene)amino]dihydrofuran-2(3H)-one as a white solid. MS M+1=356.

Workup

customthe reaction was quenched with water
extractionextracted with EtOAc
washwashed with aqueous LiCl
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
custompurified by flash chromatography (90 g silica gel, 0 to 40% EtOAc in hexane)

Sources & evidence

ORD record: ord-d9686a33c6d6490688dc73be17703e9b
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816378B2

Reaction notes

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