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

HRID 625706

반응식

HRID 625706 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 separator and the solvent removed under vacuum. The residue is purified by flash chromatography (10% ethyl acetate in cyclohexane) and then crystallized from 10% ethyl acetate in cyclohexane to give the title compound (yield 0.58 g). LC (METHOD 11): tR=6.25 min; Mass spectrum (ESI+): m/z=248 [M+H+MeCN]+.

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 separator
  6. customthe solvent removed under vacuum
  7. customThe residue is purified by flash chromatography (10% ethyl acetate in cyclohexane)
  8. customcrystallized from 10% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-4f6af052fac2458eacd2d86195962001
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09308194B2

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