Sodium hydride → Dibenzyl 2,2-di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}malonate

HRID 566494노트

반응식

HRID 566494 반응식
[C:1]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:13])[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[H-].[Na+].Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([P:35](=[O:46])([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])([F:34])[F:33])=[CH:28][CH:27]=1>CN(C=O)C>[C:42]([O:41][P:35]([C:32]([F:34])([F:33])[C:29]1[CH:30]=[CH:31][C:26]([CH2:25][C:2]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([C:32]([P:35]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:46])([F:34])[F:33])=[CH:28][CH:27]=2)([C:1]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[C:3]([O:5][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4])=[CH:27][CH:28]=1)([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:46])([CH3:43])([CH3:44])[CH3:45]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 84754Dibenzyl malonateHCID 15922636Di(tert-butyl) [4-(bromomethyl)phenyl](difluoro)methylphosphonate

생성물 1

HCID 21265761Dibenzyl 2,2-di{4-[(di-tert-butoxyphosphoryl)(difluoro)methyl]benzyl}malonate수율 18%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of dibenzyl malonate (0.5 g) in DMF (4 mL), was added sequentially NaH (0.12 g, 80% in mineral oil), di(tert-butyl) [[4-(bromomethyl)phenyl](difluoro)methyl]phosphonate (1.60 g). The reaction mixture was stirred at room temperature for 1 h, then quenched with 20 mL of saturated aqueous NH4Cl solution and extracted with 50 mL EtOAc. The extract was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 1:1 hexane/EtOAc to give the title compound (0.3 g).

후처리

  1. customquenched with 20 mL of saturated aqueous NH4Cl solution
  2. extractionextracted with 50 mL EtOAc
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluted with 1:1 hexane/EtOAc

출처 및 근거

ORD 기록
ord-88d478effc074a75b43cad65e5992102
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06174874B1

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