Sodium hydride → t-Butyl methyl 7-bromoheptylmalonate

HRID 21986

反応式

HRID 21986 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 19930816t-Butyl methyl 7-bromoheptylmalonate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e488acb45e30472096276eef2d2197a6
出典データセット
uspto-grants-1995_06
特許番号
US05426103

関連ノート

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