Sulfuric Acid → HCID 131723657, compound

HRID 1019244Notes

Reaction equation

HRID 1019244 reaction equation
[CH3:1][C:2]12[CH2:11][CH2:10][C@@H:9]([C:12]([CH3:14])=[CH2:13])[CH2:8][C:7]1=[CH:6][C:5](=[O:15])[CH2:4][CH2:3]2.S(=O)(=O)(O)[OH:17].C([O-])([O-])=O.[K+].[K+]>C(O)=O>[CH3:1][C:2]12[CH2:11][CH2:10][C@@H:9]([C:12]([OH:17])([CH3:14])[CH3:13])[CH2:8][C:7]1=[CH:6][C:5](=[O:15])[CH2:4][CH2:3]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 12069822HCID 12069822, compound

Product 1

HCID 131723657HCID 131723657, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1.2 g (5.87 mmol) of (6R/S,9R)6-Methyl-9-(1-methylvinyl)-bicyclo[4.4.0]dec-1-ene-3-one from step C of preparation A was dissolved in 20 mL of formic acid and added to 4 mL of 5% sulfuric acid solution. The reaction mixture was stirred at room temperature for 2 days, in refrigerator for 3 days, then neutralized with K2CO3 with cooling, and extracted with ethyl acetate. The extract was washed with saturated NaHCO3 solution and brine, dried, and evaporated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 5/1) to give 500 mg of product as oil and 620 mg of recovered starting material, yield 39%.

Workup

  1. temperaturewith cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated NaHCO3 solution and brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate 5/1)

Sources & evidence

ORD record
ord-0d9d27191e164c3caee520fdfcf03bb9
Source dataset
uspto-grants-2002_11
Patent number
US06486201B1

Reaction notes

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