Sodium hydride → Diethyl 2-(5-methyl-3-isoxazolyloxy)malonate

HRID 974687

反応式

HRID 974687 の反応式
[OH:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][N:3]=1.[H-].[Na+].Br[CH:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]>CN(C)P(=O)(N(C)C)N(C)C>[CH3:7][C:5]1[O:4][N:3]=[C:2]([O:1][CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:6]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 24781HymexazolHCID 69637Diethyl bromomalonate

生成物 1

HCID 19986058Diethyl 2-(5-methyl-3-isoxazolyloxy)malonate収率 84.3%

試薬・触媒・溶媒 1

HCID 12679Hexamethylphosphoramide溶媒3 回

実験手順

A solution of 3.468 g of 3-hydroxy-5-methylisoxazole in 35 ml of hexamethylphosphoric triamide was added dropwise to a suspension of 1.527 g of sodium hydride (as a 55% w/w dispersion in mineral oil) in 20 ml of hexamethylphosphoric triamide, whilst ice-cooling. The mixture was then stirred at room temperature for an hour. A solution of 8.367 g of diethyl 2-bromomalonate in 35 ml of hexamethylphosphoric triamide was then added dropwise to the mixture, whilst cooling it with ice-water. The mixture was stirred at room temperature for 1 hour and then poured into ice-water. It was then extracted twice with ethyl acetate. The combined extracts were washed with water, dried and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through 200 g of silica gel. 7.593 g of the title compound were isolated as an oily material from the fractions eluted with mixtures of ethyl acetate and hexane ranging from 1:10 to 15:100 by volume.

後処理

  1. temperaturewhilst ice-cooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. extractionIt was then extracted twice with ethyl acetate
  4. washThe combined extracts were washed with water
  5. customdried
  6. concentrationconcentrated by evaporation under reduced pressure

出典と根拠

ORDレコード
ord-7c04a3f073da463090f6d9c379a1b280
出典データセット
uspto-grants-1991_11
特許番号
US05068340

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