Acetic Acid → 2(1H)-Pentalenone, 5-(benzoyloxy)hexahydro-4-(hydroxymethyl)-, [3aS-(3aα,4α,5β,6aα)]-

HRID 2309133Notes

Reaction equation

HRID 2309133 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:13][CH2:14][CH3:15])(=O)C.[C:16]([OH:19])(=O)[CH3:17]>[Pd]>[C:1]([O:9][C@@H:6]1[CH2:7][C@H:2]2[C@H:3]([CH2:4][C:16](=[O:19])[CH2:17]2)[C@H:15]1[CH2:14][OH:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 242BenzoateHCID 8857Ethyl Acetate

Product 1

HCID 228220742(1H)-Pentalenone, 5-(benzoyloxy)hexahydro-4-(hydroxymethyl)-, [3aS-(3aα,4α,5β,6aα)]-

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 680 mg. of the benzoate prepared according to Reference Example 1(n) in 10 ml. of ethyl acetate and 0.5 ml. of glacial acetic acid acid is combined with 120 mg. of palladium on charcoal (10%) and shaken for 8 hours under a hydrogen atmosphere. Filtration and evaporation of the solution under vacuum yields 600 mg. of an oily crude product, which is purified by chromatography on silica gel with pentane/ethyl acetate (1+1), and 395 mg. of the pure alcohol as a colorless oil.

Workup

  1. filtrationFiltration and evaporation of the solution under vacuum
  2. customyields 600 mg
  3. customof an oily crude product, which is purified by chromatography on silica gel with pentane/ethyl acetate (1+1), and 395 mg

Sources & evidence

ORD record
ord-a771590e8607447fb579d4c394d9f864
Source dataset
uspto-grants-1987_09
Patent number
US04692464

Reaction notes

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