Potassium Hydroxide → HCID 58604048, compound

HRID 2113674Notes

Reaction equation

HRID 2113674 reaction equation
[CH2:1]([C:5]1([CH2:20][C:21](=[O:23])[CH3:22])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([F:18])=[C:10]([O:16][CH3:17])[C:11]=2[Cl:15])[C:6]1=O)[CH2:2][CH2:3][CH3:4].[OH-].[K+]>CCO.ClCCl>[CH2:1]([C:5]12[CH2:20][C:21](=[O:23])[CH:22]=[C:6]1[C:7]1[C:12]([CH2:13][CH2:14]2)=[C:11]([Cl:15])[C:10]([O:16][CH3:17])=[C:9]([F:18])[CH:8]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 58604070HCID 58604070, compound

Product 1

HCID 58604048HCID 58604048, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-butyl-5-chloro-7-fluoro-6-methoxy-2-(2-oxo-propyl)-3,4-dihydro-2H-naphthalen-1-one (28 mg, 0.08 mmol) in EtOH (0.4 mL) was added potassium hydroxide (2M solution in EtOH, 0.05 mL, 0.1 mmol). The reaction mixture was heated at 90° C. in a sealed flask for two hours. The reaction was cooled to room temperature, diluted with dichloromethane (5 mL) and filtered through a pad of MgSO4 atop a pad of SiO2. The filter pad was washed with 5% MeOH in CH2Cl2 and the combined filtrates concentrated under vacuum to give 3a-butyl-6-chloro-8-fluoro-7-methoxy-3,3a,4,5-tetrahydro-2H-cyclopenta[a]naphthalen-2-one as an oil which solidified on standing.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through a pad of MgSO4 atop a pad of SiO2
  3. washThe filter pad was washed with 5% MeOH in CH2Cl2
  4. concentrationthe combined filtrates concentrated under vacuum

Sources & evidence

ORD record
ord-40238db2869240caa73361a942729609
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

Loading…