Propargyl alcohol → tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(propargyloxy-carbonyl)-ethenyl]cyclopropane-carboxylate
Reaction equation
[CH3:1][C:2]1([CH3:17])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([OH:9])=[O:8])[C@H:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[CH2:18](O)[C:19]#[CH:20]>>[CH3:1][C:2]1([CH3:17])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH2:20][C:19]#[CH:18])=[O:8])[C@H:3]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]Participants
Conditions
- Temperature
- 20 °C
Procedure
Using the procedure of Step A of Example 13, 3.6 g of tert.-butyl (1R,cis) 2,2-dimethyl-3-[Z-2-carboxy-ethenyl]-cyclopropane-carboxylate and 1 ml of propargyl alcohol were reacted and the mixture was stirred at 20° C. for 16 hours and was filtered. The filtrate was extracted with methylene chloride and the organic phase was washed with 0.1 N hydrochloric acid, with water until the wash water was neutral, dried and evaporated to dryness under reduced pressure. The residue was taken up in a 9-1 cyclohexane-ethyl acetate mixture and the mixture was stirred at 20° C. for 90 minutes and was filtered. The filtrate was evaporated to dryness and the residue was chromatographed over silica gel. Elution with a 9-1 cyclohexane-ethyl acetate yielded 2.1 g of tert.-butyl (1R,cis) 2,2-dimethyl-3-[Z-2-(propargyloxy-carbonyl)-ethenyl]-cyclopropane-carboxylate.
Workup
- customwere reacted
- filtrationwas filtered
- extractionThe filtrate was extracted with methylene chloride
- washthe organic phase was washed with 0.1 N hydrochloric acid, with water until the wash water
- customdried
- customevaporated to dryness under reduced pressure
- stirringthe mixture was stirred at 20° C. for 90 minutes
- filtrationwas filtered
- customThe filtrate was evaporated to dryness
- customthe residue was chromatographed over silica gel
- washElution with a 9-1 cyclohexane-ethyl acetate
Sources & evidence
- ORD record
- ord-72ba5b5532844cc0a66d893125772812
- Source dataset
- uspto-grants-1983_09
- Patent number
- US04402972
Reaction notes
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