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

HRID 1160179노트

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HRID 1160179 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d9686a33c6d6490688dc73be17703e9b
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07816378B2

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