Sodium hydride → t-Butyl methyl 7-bromoheptylmalonate

HRID 21986

반응식

HRID 21986 반응식
[H-].[Na+].[C:3]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br>CN(C)C=O>[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:4]([C:5]([O:7][CH3:8])=[O:6])[C:3]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 783091,7-DibromoheptaneHCID 2733872tert-Butyl methyl malonate

생성물 1

HCID 19930816t-Butyl methyl 7-bromoheptylmalonate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium hydride (3.04 g of a 50% oil dispersion, 127 mmol) is suspended in dimethylformamide (300 ml) and the suspension is cooled to 0° C. t-Butyl methyl malonate (20.08 g, 115 mmol) is added dropwise slowly and the reaction mixture is warmed to room temperature. 1,7-Dibromoheptane (29.75 g, 115 mmol) is added dropwise and the mixture is stirred for 3 hours. The mixture is partitioned between diethyl ether (500 ml) and water (1000 ml). The organic layer is washed with water (3×500 ml), brine (1×500 ml), dried (MgSO4) and the solvent is evaporated. The product is purified by silica gel chromatography (10% ethyl acetate/hexane) to give t-butyl methyl 7-bromoheptylmalonate as an oil.

후처리

  1. additionis added dropwise slowly
  2. customThe mixture is partitioned between diethyl ether (500 ml) and water (1000 ml)
  3. washThe organic layer is washed with water (3×500 ml), brine (1×500 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent is evaporated
  6. customThe product is purified by silica gel chromatography (10% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-e488acb45e30472096276eef2d2197a6
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426103

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