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 0.1N 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 0.1N 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-60b4d0f0ed7c48dfa87de9132953677e
- Source dataset
- uspto-grants-1985_10
- Patent number
- US04547522
Reaction notes
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