Reaction equation
[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([CH3:19])=[C:13]1[C:12]1[C:7](=[C:8]([Cl:22])[C:9]([O:20]C)=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4].Cl.N1C=CC=CC=1>>[CH2:1]([C:5]12[CH2:17][CH2:16][C:15](=[O:18])[C:14]([CH3:19])=[C:13]1[C:12]1[C:7](=[C:8]([Cl:22])[C:9]([OH:20])=[CH:10][CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]Participants
Conditions
- Temperature
- 195 °C
Procedure
A mixture of 9a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (36.6 mg) and pyridine hydrochloride (2.66) was stirred and heated in an oil bath at 190-200° C. for 80 minutes. After cooling to room temperature, the mixture was partitioned between EtOAc (20 mL) and water (30 mL). The organic phase was washed with brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 10% EtOAc in CH2Cl2. The UV visible product band was eluted with EtOAc, the eluant evaporated under vacuum, and the residue lyophilized from benzene to afford 9a-butyl-8-chloro-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous solid.
Workup
- temperatureAfter cooling to room temperature
- customthe mixture was partitioned between EtOAc (20 mL) and water (30 mL)
- washThe organic phase was washed with brine (10 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated under vacuum
- customThe residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate
- washThe UV visible product band was eluted with EtOAc
- customthe eluant evaporated under vacuum
Sources & evidence
- ORD record
- ord-e71cb2ebf2654d4ba5d844ad5a953bf8
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087599B2
Linked notes
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