1,5-Dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one → HCID 13534071, compound

HRID 1583860Notes

Reaction equation

HRID 1583860 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]2

Participants

4

Reactant 2

HCID 135340701,5-Dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 13534071HCID 13534071, compoundYield 128.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

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.

Workup

  1. washwashed successively with water (2.5 ml), 15% aqueous sodium hydroxide (2.5 ml) and water (7.5 ml)
  2. filtrationfiltered
  3. washThe filter cake was washed with diethyl ether
  4. dry with materialthe combined ether filtrates were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-11d08819028b468e9372e7f0eae8a6f7
Source dataset
uspto-grants-1985_11
Patent number
US04554366

Reaction notes

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