Water → 1,8,8-Trimethyl-2-oxa bicyclo [3,2,1] octan-3-ol

HRID 615839Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][C:12]12[C:19]([CH3:21])([CH3:20])[CH:16]([CH2:17][CH2:18]1)[CH2:15][C:14](=[O:22])[O:13]2.O>C1(C)C=CC=CC=1>[CH3:11][C:12]12[C:19]([CH3:21])([CH3:20])[CH:16]([CH2:17][CH2:18]1)[CH2:15][CH:14]([OH:22])[O:13]2

Participants

Conditions

Temperature: -60 °C

Procedure

25 ml of a solution of 1.1M of diisobutylaluminum hydride in toluene was added at -60° C. over 90 minutes to a solution of 5 g of 1,8,8-trimethyl-2-oxa-bicyclo [3,2,1] octane-3-one [process of Ronald et al, J.A.C.S., Vol. 81 (1959), p. 925] in 20 ml of toluene and the mixture was stirred for 2 hours at -60° C. Water was added dropwise while the temperature was allowed to rise to 20° C. and the mixture was then stirred at 20° C. for 2 hours. The mixture was filtered to remove lithium salts and the filter was washed with methylene chloride. The decanted aqueous phase of the filtrate was extracted with methylene chloride. The organic phase was dried and evaporated to dryness and the residue was chromatographed over silica gel. Elution with a 1--1 benzene-ethyl acetate mixture yielded 3.5 g of 1,8,8-trimethyl-2-oxa-bicyclo [3,2,1] octan-3-ol.

Workup

customto rise to 20° C.
stirringthe mixture was then stirred at 20° C. for 2 hours
filtrationThe mixture was filtered
customto remove lithium salts
washthe filter was washed with methylene chloride
extractionThe decanted aqueous phase of the filtrate was extracted with methylene chloride
customThe organic phase was dried
customevaporated to dryness
customthe residue was chromatographed over silica gel
washElution with a 1--1 benzene-ethyl acetate mixture

Sources & evidence

ORD record: ord-699995d1644148808c90ab65cceee9a2
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04501687

Reaction notes

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