Acetic Acid → 5-Hydroxy-hexahydro-pentalen-2-one

HRID 1660297Notes

Reaction equation

HRID 1660297 reaction equation
[BH4-].[Na+].[CH:3]12[CH2:10][C:9](=[O:11])[CH2:8][CH:7]1[CH2:6][C:5](=[O:12])[CH2:4]2.CC(C)=O.C(O)(=O)C>C(Cl)Cl.C(O)C.O>[OH:12][CH:5]1[CH2:4][CH:3]2[CH:7]([CH2:8][C:9](=[O:11])[CH2:10]2)[CH2:6]1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 103526cis-Tetrahydropentalene-2,5(1H,3H)-dioneHCID 4311764Sodium borohydride

Product 1

HCID 130418335-Hydroxy-hexahydro-pentalen-2-oneYield 77.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

1.1 g of sodium borohydride (0.029 mol) is added with stirring to a solution of 11.6 g of bicyclo[3.3.0]octane-3,7-dione (8.4×10-2 mol) in 100 ml of methylene chloride and 100 ml of ethanol. After 45 minutes at this temperature, the excess reagent is decomposed by slowly adding 20 ml of acetone. The mixture is then neutralized with 1.4 ml of acetic acid, and evaporated under vacuum to afford a residue which is taken up in water and methylene chloride. The organic phase is evaporated to dryness and filtered on silica gel (70:30 hexane:ethyl ether as eluent) to afford 9.1 g of 7ξ-hydroxy-bicyclo[3.3.0]octan-3-one.

Workup

  1. customevaporated under vacuum
  2. customto afford a residue which
  3. customThe organic phase is evaporated to dryness
  4. filtrationfiltered on silica gel (70:30 hexane:ethyl ether as eluent)

Sources & evidence

ORD record
ord-a903e17f43fe4c0a97a3f61c7791fb6d
Source dataset
uspto-grants-1981_12
Patent number
US04307112

Reaction notes

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