Hydrochloric Acid → 9a-butyl-7-hydroxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7863Notes

Reaction equation

HRID 7863 reaction equation
[CH2:1]([C:5]12[CH2:17][C:16]([CH3:19])([CH3:18])[C:15](=[O:20])[C:14]([CH3:21])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([O:22]COC)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].Cl.C([O-])(O)=O.[Na+]>CO.CCOC(C)=O>[CH2:1]([C:5]12[CH2:17][C:16]([CH3:19])([CH3:18])[C:15](=[O:20])[C:14]([CH3:21])=[C:13]1[C:12]1[C:7](=[CH:8][C:9]([OH:22])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 219908699a-butyl-7-methoxymethoxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Product 1

HCID 99222999a-butyl-7-hydroxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
67.5 °C

Procedure

A solution of 9a-butyl-7-methoxymethoxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (28 mg, 0.08 mmol) in methanol (2 mL) was placed under a nitrogen atmosphere and treated with 2N aqueous HCl (0.12 mL, 0.24 mmol). The resulting yellow solution was stirred and heated in an oil bath at 55-80° C. for 45 minutes. After cooling to room temperature, the mixture was diluted with EtOAc (60 mL) and shaken with 5% aqueous NaHCO3. The aqueous portion was separated and extracted with EtOAc (40 mL). The combined organics were washed with water and brine, dried over MgSO4, filtered, and concentrated under vacuum to an oil. The crude product was purified by PLC on a 0.1×20×20 cm silica gel GF plate, developing twice with 4:1 hexanes-EtOAc. The band at Rf 0.34-0.43 was eluted with EtOAc and the eluant evaporated under vacuum to a residue which was lyophilized from benzene to afford 9a-butyl-7-hydroxy-2,2,4-trimethyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe aqueous portion was separated
  3. extractionextracted with EtOAc (40 mL)
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum to an oil
  8. customThe crude product was purified by PLC on a 0.1×20×20 cm silica gel GF plate
  9. washThe band at Rf 0.34-0.43 was eluted with EtOAc
  10. customthe eluant evaporated under vacuum to a residue which

Sources & evidence

ORD record
ord-b696197867354374bb82affcc3d1f4f4
Source dataset
uspto-grants-2006_08
Patent number
US07087599B2

Reaction notes

Loading…