1,5-Dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one → HCID 13534071, compound
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]12[O:15][C:12]([CH3:16])([CH:13]=[CH:14]1)[CH2:11][C:10](=[O:17])[CH2:9]2>C(OCC)C>[CH3:16][C:12]12[O:15][C:8]([CH3:7])([CH:14]=[CH:13]1)[CH2:9][CH:10]([OH:17])[CH2:11]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred suspension of lithium aluminum hydride (4.6 g of a 57% oil suspension) in dry diethyl ether (300 ml) was added a solution of 1,5-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one (10.0 g) in diethyl ether (50 ml) over 0.5 hour at 20° C. The reaction mixture was held for 2 hours at 20° C., cooled to 0° C., and washed successively with water (2.5 ml), 15% aqueous sodium hydroxide (2.5 ml) and water (7.5 ml), and filtered. The filter cake was washed with diethyl ether, and the combined ether filtrates were dried (MgSO4), filtered and concentrated to give 13.0 g of oil. The oil was eluted through a column of florisil first with hexane and then diethyl ether. The ether fractions were combined and concentrated to give the desired product (10.0 g) as a 66:34 mixture of epimers.