Hydrochloric Acid → (2-phenoxy-5-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane-1-carboxylate

HRID 544435Notes

Reaction equation

[O:1]([C:8]1[S:9][C:10]([CH2:13][OH:14])=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]1([CH3:26])[C@@H:18]([CH:19]=[C:20]([CH3:22])[CH3:21])[C@H:17]1[C:23](Cl)=[O:24].Cl>C1C=CC=CC=1.N1C=CC=CC=1>[CH3:15][C:16]1([CH3:26])[C@@H:18]([CH:19]=[C:20]([CH3:21])[CH3:22])[C@H:17]1[C:23]([O:14][CH2:13][C:10]1[S:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:12][CH:11]=1)=[O:24]

Participants

Conditions

Temperature: 20 °C

Procedure

2.07 g of (2-phenoxy-5-thiazolyl)-methanol were added to a solution of (1R,3S) 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane-1-carboxylic acid chloride prepared from 1.68 g of the corresponding acid in 20 ml of benzene and 0.81 ml of pyridine were added dropwise thereto. The mixture was stirred at 20° C. for 17 hours and was poured into dilute aqueous hydrochloric acid. The decanted aqueous phase was extracted with ether and the combined organic phases were washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and eluted with an 8-2 cyclohexane-ethyl acetate mixture to obtain 1.6 g of (2-phenoxy-5-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane -1-carboxylate.

Workup

additionwere added dropwise
extractionThe decanted aqueous phase was extracted with ether
washthe combined organic phases were washed with water
customdried
customevaporated to dryness under reduced pressure
customThe residue was chromatographed over silica gel
washeluted with an 8-2 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record: ord-e32ba24ffaca476081d2155d6e53b66a
Source dataset: uspto-grants-1984_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04450169

Reaction notes

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