Water → Ethyl 5-(bromomethyl)-1,2-oxazole-3-carboxylate

HRID 58525

反応式

HRID 58525 の反応式
Cl[C:2](=[N:8][OH:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:10][CH2:11][C:12]#[CH:13].C(=O)(O)[O-].[Na+].O>C(OCC)(=O)C>[Br:10][CH2:11][C:12]1[O:9][N:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:13]=1

参加物

6

反応物 4

HCID 962WaterHCID 7842Propargyl bromideHCID 516892Sodium BicarbonateHCID 6816376Ethyl chloro(hydroximino)acetate

生成物 1

HCID 13124955Ethyl 5-(bromomethyl)-1,2-oxazole-3-carboxylate収率 87.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

A solution of ethyl 2-chloro-2-(hydroxyimino)acetate (11 g; 70.41 mmol) in ethyl acetate (60 mL) was added dropwise at room temperature to a mixture of 3-bromoprop-1-yne (15.2 mL; 141 mmol), sodium bicarbonate (11.95 g; 141 mmol), ethyl acetate (400 mL), and water (4 mL). The mixture was stirred at room temperature for 24 h and the solid was removed by filtration and washed with ethyl acetate. The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (eluent: 15 to 100% of dichloromethane in heptane) to give 14.38 g (87%) of ethyl 5-(bromomethyl)isoxazole-3-carboxylate as a white solid.

後処理

  1. customthe solid was removed by filtration
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel (eluent: 15 to 100% of dichloromethane in heptane)

出典と根拠

ORDレコード
ord-bb9378b602534687974a7e8d0a1bf5e2
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

関連ノート

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