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

HRID 566501노트

반응식

HRID 566501 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:44]=[CH:43][C:29]([CH2:30][P:31](=[O:42])([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:28][CH:27]=1>CN(C=O)C>[C:38]([O:37][P:31]([CH2:30][C:29]1[CH:43]=[CH:44][C:26]([CH2:25][CH: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:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:42])([CH3:39])([CH3:40])[CH3:41]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 84754Dibenzyl malonateHCID 10915802Di(tert-butyl) [4-(bromomethyl)benzyl]phosphonate

생성물 1

HCID 21265737Dibenzyl 2-{4-[(di-tert-butoxyphosphoryl)methyl]benzyl}malonate수율 19.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of dibenzyl malonate (0.5 g) in DMF (8 mL), was added sequentially NaH (0.06 g, 80% in mineral oil), di(tert-butyl) [4-(bromomethyl)benzyl]phosphonate(0.66 g). The reaction mixture was stirred at room temperature for 1 h, then quenched with 20 mL of saturated aqueous NH4OAc solution and extracted with 50 mL EtOAc. The extract was dried over Na2SO4 and concentrated. The sesidue was purified by silica gel chromatography eluted with to give the title compound (0.2 g).

후처리

  1. customquenched with 20 mL of saturated aqueous NH4OAc solution
  2. extractionextracted with 50 mL EtOAc
  3. dry with materialThe extract was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe sesidue was purified by silica gel chromatography
  6. washeluted with

출처 및 근거

ORD 기록
ord-e108d89f32b94dd19a3d3fd22ebc4a9d
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06174874B1

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