Dichloromethane → 2,2-dimethyl-3-[(Z)-2-(methoxy carbonyl)-ethenyl]-cyclopropane-carboxylic acid
Reaction equation
[CH3:1][C:2]1([CH3:17])[C@@H:4]([C:5]#[C:6][C:7]([OH:9])=[O:8])[C@H:3]1[C:10]([O:12]C(C)(C)C)=[O:11].[CH2:18](Cl)Cl>CN(C)C1C=CN=CC=1.C(O)C>[CH3:1][C:2]1([CH3:17])[CH:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH3:18])=[O:8])[CH:3]1[C:10]([OH:12])=[O:11]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
4 g of the product of Step A, 3.4 g of dicyclohexylcarbodiiumide and 6 mg of 4-dimethylamino-pyridine were added to 30 ml of methylene chloride followed by the addition of 1.5 ml of ethanol and the mixture was stirred at 20° C. for 16 hours. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 9-1 cyclohexane-ethyl acetate mixture to obtain 4.25 g of tert.butyl (1R, cis) 2,2-dimethyl-3-(ethoxycarbonyl-ethynyl)-cyclopropane-carboxylate.
Workup
- filtrationThe mixture was filtered
- customthe filtrate was evaporated to dryness under reduced pressure
- customThe residue was chromatographed over silica gel
- washwas eluted with a 9-1 cyclohexane-ethyl acetate mixture
Sources & evidence
- ORD record
- ord-c7527883d4d94f11829e54a1ccb523ec
- Source dataset
- uspto-grants-1983_09
- Patent number
- US04402972
Reaction notes
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