Hydrochloric Acid → HCID 22840735, compound

HRID 256228Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]1([CH3:23])[C@H:17]2[C@@H:13]1[C@H:14]([C:19]([Cl:22])([Cl:21])[Cl:20])[O:15][C:16]2=[O:18].Cl>C1(C)C=CC=CC=1>[CH3:11][C:12]1([CH3:23])[C@H:17]2[C@@H:13]1[C@H:14]([C:19]([Cl:22])([Cl:20])[Cl:21])[O:15][C@@H:16]2[OH:18]

Participants

Conditions

Temperature: -60 °C

Procedure

75 ml of a toluene solution of 20% of diisobutylaluminum hydride were slowly added at -60° C. to a solution of 20 g of (1R,4R,5S) 6,6-dimethyl-4-trichloromethyl-3-oxa-bicyclo(3,1,0)-hexane-2-one in 200 ml of toluene and the mixture was stirred at -60° C. for one hour and was poured into an ice-water mixture. Aqueous N hydrochloric acid was added to the mixture to adjust the pH to 3 to 4 and the mixture was filtered. The decanted benzene phase was washed with aqueous sodium bicarbonate solution, with water and evaporated to dryness under reduced pressure. The residue was added to petroleum ether (b.p.=35°-70° C.) and the mixture was filtered to obtain 14.5 g of (1R,2S,4R,5S) 6,6-dimethyl-4-trichloromethyl-3-oxa-bicyclo(3,1,0)hexan-2-ol melting at 140° C.

Workup

filtrationthe mixture was filtered
washThe decanted benzene phase was washed with aqueous sodium bicarbonate solution, with water
customevaporated to dryness under reduced pressure
additionThe residue was added to petroleum ether (b.p.=35°-70° C.)
filtrationthe mixture was filtered

Sources & evidence

ORD record: ord-9285ee7d6afa4e3e89cd92780bf282b1
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04701542

Reaction notes

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