Pyridinium chloride → 9a-butyl-8-chloro-6-fluoro-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one
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:23])[C:9]([O:21]C)=[C:10]([F:20])[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:23])[C:9]([OH:21])=[C:10]([F:20])[CH:11]=1)[CH2:6]2)[CH2:2][CH2:3][CH3:4]Participants
Conditions
- Temperature
- 200 °C
Procedure
The product mixture from step 3 and pyridine hydrochloride (5.3 g) were combined and heated in an oil bath at 200° C. for 90 minutes. After cooling, the mixture was partitioned between EtOAc (50 mL) and water (50 ml). The organic phase was washed with brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to a blue oil. The oil was purified by preparative layer chromatography on four 0.05×20×20 silica gel GF plates, developing with 5% EtOAc in CH2Cl2. One of the plates was discarded due to excessive streaking. The combined product bands were eluted with EtOAc, the eluent evaporated under vacuum, and the residue lyophilized from benzene (3 mL) containing EtOH (2 drops) to afford 9a-butyl-8-chloro-6-fluoro-7-hydroxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one as an amorphous solid.
Workup
- temperatureAfter cooling
- customthe mixture was partitioned between EtOAc (50 mL) and water (50 ml)
- washThe organic phase was washed with brine (50 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated under vacuum to a blue oil
- customThe oil was purified by preparative layer chromatography on four 0.05×20×20 silica gel GF plates
- washThe combined product bands were eluted with EtOAc
- customthe eluent evaporated under vacuum
- additioncontaining EtOH (2 drops)
Sources & evidence
- ORD record
- ord-3ce351c7b8ea4f2facd72afa9105e46c
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087599B2
Reaction notes
Loading…