Sodium hydride → t-Butyl methyl 7-bromoheptylmalonate

HRID 21986

Reaction equation

HRID 21986 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 19930816t-Butyl methyl 7-bromoheptylmalonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-e488acb45e30472096276eef2d2197a6
Source dataset
uspto-grants-1995_06
Patent number
US05426103

Linked notes

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