Ethanol → (1R,2R)-ethyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate

HRID 471426

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HRID 471426 반응식
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=1)=[O:5])[CH3:2].B(Br)(Br)Br.C(O)C>ClCCl.C(=O)(O)[O-].[Na+]>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)=[O:5])[CH3:2]

참가 물질

6

반응물 3

HCID 702EthanolHCID 25134Boron tribromideHCID 818082rac-ethyl (1R,2R)-2-(4-methoxyphenyl)cyclopropane-1-carboxylate

생성물 1

HCID 71114948(1R,2R)-ethyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate수율 43.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
-78 °C

실험 절차

2-(4-Methoxy-phenyl)-trans-cyclopropanecarboxylic acid ethyl ester (1.43 g, 6.51 mmol) is dissolved in dry dichloromethane (30 mL) and cooled to −78° C. Boron tribromide solution (1 M in dichloromethane, 7.81 mL, 7.81 mmol) is added dropwise then the mixture is allowed to warm to −20° C. and stirred overnight at −20° C. Ethanol (3 mL) is added and the mixture warmed to room temperature then diluted with saturated aqueous sodium bicarbonate solution. The phases are separated and the aqueous phase extracted with dichloromethane. The combined organic phases are dried through a phase seperator and the solvent removed under vacuum. The residue is purified by flash chromatography (10% ethyl acetate in cyclohexane) and then crystallised from 10% ethyl acetate in cyclohexane to give the title compound (yield 0.58 g).

후처리

  1. temperatureto warm to −20° C.
  2. temperaturethe mixture warmed to room temperature
  3. customThe phases are separated
  4. extractionthe aqueous phase extracted with dichloromethane
  5. customThe combined organic phases are dried through a phase seperator
  6. customthe solvent removed under vacuum
  7. customThe residue is purified by flash chromatography (10% ethyl acetate in cyclohexane)
  8. customcrystallised from 10% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-2374fc4e28124b14ba9b7d49f1565e70
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633182B2

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