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

HRID 58525

반응식

HRID 58525 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-bb9378b602534687974a7e8d0a1bf5e2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

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