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

HRID 2198812Notes

Reaction equation

HRID 2198812 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 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-75a3a91faddc467d8d16470d56f1a0af
Source dataset
uspto-grants-1982_11
Patent number
US04359581

Reaction notes

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