Ethanol → HCID 86740519, compound

HRID 637322

Reaction equation

[CH3:1][C:2]1([CH3:14])[CH:4]([CH:5]=O)[CH:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[O:15]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)C.[Na]>O.C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:14])[C@H:4]([CH:5]=[C:22]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[C@H:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

Conditions

Temperature: 20 °C

Procedure

9.9 g of tert.-butyl 2,2-dimethyl-3-formyl-cyclopropane-carboxylate and 28 g of ethyl phenoxyacetate were added dropwise at 0° C. to a mixture of 0.05 ml of ethanol, 1.25 g of sodium in small pieces and 25 ml of toluene and the solution was stirred at 20° C. for 16 hours. 20 ml of toluene were added thereto and the mixture was stirred for 4 hours and was poured into iced water. The mixture was extracted with methylene chloride and the organic phase was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 7-3 hexane-ethyl acetate mixture to obtain 12.47 g of E or Z isomer of tert.-butyl (1R,trans) 2,2-dimethyl-3-[2-phenoxy-2-ethoxycarbonyl-ethenyl]-cyclopropane-carboxylate.

Workup

stirringthe mixture was stirred for 4 hours
extractionThe mixture was extracted with methylene chloride
customthe organic phase was evaporated to dryness under reduced pressure
customThe residue was chromatographed over silica gel
washwas eluted with a 7-3 hexane-ethyl acetate mixture

Sources & evidence

ORD record: ord-805ed1e8cbb24b90a570527abb9e86ae
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04556666

Linked notes

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