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

HRID 238170ノート

反応式

HRID 238170 の反応式
[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

参加物

7

反応物 4

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 24823Ozone2 回HCID 546367Cyclopropanecarboxylic acid, 1-(2-propenyl)-, 1,1-dimethylethyl ester

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-207b2a0e02ac43db874ec8f41379d8dc
出典データセット
uspto-grants-2014_02
特許番号
US08642592B2

反応ノート

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