Oxygen → Tert-Butyl 1-(2-oxoethyl)cyclopropanecarboxylate

HRID 238170

반응식

HRID 238170 반응식
[CH2:1]([C:4]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5]1)[CH:2]=C.[O:14]=[O+][O-].O=O.CSC>CO.ClCCl>[O:14]=[CH:2][CH2:1][C:4]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5]1

참가 물질

7

반응물 4

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 24823Ozone2회HCID 546367Cyclopropanecarboxylic acid, 1-(2-propenyl)-, 1,1-dimethylethyl ester

생성물 1

HCID 58817571Tert-Butyl 1-(2-oxoethyl)cyclopropanecarboxylate

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

4.0 g (21.9 mmol) of tert-butyl 1-(prop-2-en-1-yl)cyclopropanecarboxylate were dissolved in 70 ml of methanol and 30 ml of dichloromethane. At −78° C., ozone in a stream of O2 was passed through the reaction solution for 45 min using an ozone generator. Once the color of the solution had changed to light blue, the reaction solution was flushed with pure oxygen until the color had disappeared again. 6.5 ml (88.9 mmol) of dimethyl sulfide were then added, and the reaction solution was slowly warmed to RT. The mixture was concentrated on a rotary evaporator and the residue was purified by chromatography on silica gel (mobile phase gradient cyclohexane/ethyl acetate 50:1, 30:1, 20:1, 10:1). This gave 1.87 g (44.1% of theory) of the target compound.

후처리

  1. customwas flushed with pure oxygen until the color
  2. concentrationThe mixture was concentrated on a rotary evaporator
  3. customthe residue was purified by chromatography on silica gel (mobile phase gradient cyclohexane/ethyl acetate 50:1, 30:1, 20:1, 10:1)

출처 및 근거

ORD 기록
ord-207b2a0e02ac43db874ec8f41379d8dc
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642592B2

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