HCID 13924131, compound → (3aR,7aS)-4,4,7a-trimethyl-3a,5,6,7-tetrahydro-3H-1-benzofuran-2-one

HRID 1789248Notes

Reaction equation

HRID 1789248 reaction equation
[O:1]=[C:2]1[CH2:6][C@@H:5]2[C:7]([CH3:12])([CH3:11])[CH:8]=[CH:9][CH2:10][C@:4]2([CH3:13])[O:3]1>C(O)(=O)C.[Pt]=O>[O:1]=[C:2]1[CH2:6][C@@H:5]2[C:7]([CH3:12])([CH3:11])[CH2:8][CH2:9][CH2:10][C@:4]2([CH3:13])[O:3]1

Participants

4

Reactant 1

HCID 13924131HCID 13924131, compound

Product 1

HCID 11074042(3aR,7aS)-4,4,7a-trimethyl-3a,5,6,7-tetrahydro-3H-1-benzofuran-2-oneYield 90%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

Compound (13) (1.00 g, 5.55 mmoles) was dissolved in dry acetic acid, and platinum oxide (0.10 g) was added to the solution. The mixture was shaken for 23 hours under hydrogen pressure (30 atms.). The catalyst was separated by filtration, and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate, and the ethyl acetate solution was washed with an aqueous solution of sodium hydrogen-carbonate, water and an aqueous solution of sodium chloride in this order, dried over magnesium sulfate, and concentrated under vacuum. The residue was purified by column chromatography (10 g of silica gel; n-hexane/ethyl acetate) to give crystalline (3aR,7aS)-isomer (14) (0.910 g, yield 80%). Recrystallization from n-hexane gave 0.669 g of the purified compound (14).

Workup

  1. customThe catalyst was separated by filtration
  2. concentrationthe filtrate was concentrated under vacuum
  3. additionThe residue was diluted with ethyl acetate
  4. washthe ethyl acetate solution was washed with an aqueous solution of sodium hydrogen-carbonate, water
  5. dry with materialan aqueous solution of sodium chloride in this order, dried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography (10 g of silica gel; n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2f90b6dd5c40496aa3109111541eaee4
Source dataset
uspto-grants-1987_08
Patent number
US04687863

Reaction notes

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