Hydrochloric Acid → HCID 9971139, compound

HRID 2113666Notes

Reaction equation

HRID 2113666 reaction equation
[CH2:1]([C:5]12[CH2:22][C:21](=[O:23])[C:20]([CH3:24])=[C:6]1[C:7]1[C:12]([CH2:13][CH2:14]2)=[C:11]([CH3:15])[C:10]([O:16]COC)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4].Cl>CO.CCOC(C)=O>[CH2:1]([C:5]12[CH2:22][C:21](=[O:23])[C:20]([CH3:24])=[C:6]1[C:7]1[C:12]([CH2:13][CH2:14]2)=[C:11]([CH3:15])[C:10]([OH:16])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58604061HCID 58604061, compound

Product 1

HCID 9971139HCID 9971139, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3a-butyl-7-(methoxymethoxy)-1,6-dimethyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one (63 mg, 0.19 mmol) in methanol (1.1 mL) was treated with aqueous 2N HCl (0.3 mL), placed under a N2 atmosphere, stirred, and heated in an oil bath at 80° C. for 35 minutes. After cooling, the mixture was diluted with EtOAc (25 mL) and washed with 5% NaHCO3 (10 mL). The organic phase was dried over MgSO4, filtered, and evaporated under vacuum to provide 3a-butyl-7-hydroxy-1,6-dimethyl-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one as a solid.

Workup

  1. temperatureAfter cooling
  2. washwashed with 5% NaHCO3 (10 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-fdef6c8613e4434080d522638fde8c41
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

Loading…