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

HRID 238170

Reaction equation

HRID 238170 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-207b2a0e02ac43db874ec8f41379d8dc
Source dataset
uspto-grants-2014_02
Patent number
US08642592B2

Linked notes

Loading…