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

HRID 1160179ノート

反応式

HRID 1160179 の反応式
[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

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 132309163-[(diphenylmethylene)amino]dihydrofuran-2(3H)-one

生成物 1

HCID 866323393-benzyl-3-[(diphenylmethylene)amino]dihydrofuran-2(3H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-d9686a33c6d6490688dc73be17703e9b
出典データセット
uspto-grants-2010_10
特許番号
US07816378B2

反応ノート

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