Reaction equation
Br[C:2]1[C:3](=[O:21])[CH2:4][CH2:5][C:6]2([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]=1[C:13]1[C:8](=[CH:9][C:10]([O:15][CH3:16])=[CH:11][CH:12]=1)[CH2:7]2.[Cu][C:23]#[N:24]>CN1CCCC1=O>[CH2:17]([C:6]12[CH2:5][CH2:4][C:3](=[O:21])[C:2]([C:23]#[N:24])=[C:14]1[C:13]1[C:8](=[CH:9][C:10]([O:15][CH3:16])=[CH:11][CH:12]=1)[CH2:7]2)[CH2:18][CH2:19][CH3:20]Participants
4
Conditions
- Temperature
- 160 °C
Procedure
A solution of 4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (50 mg, 0.138 mmol) in anhydrous 1-methyl-2-pyrrolidinone (0.276 mL) was treated with copper(I) cyanide (25 mg, 0.275 mmol). The resulting mixture was stirred under a nitrogen atmosphere and heated in an oil bath at 160° C. for 40 minutes. The mixture was partitioned between EtOAc (20 mL) and water (20 ml). The organic phase was washed with water (2×20 mL) and 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 5% EtOAc in CH2Cl2, to afford 9a-butyl-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (33 mg) as an oil.
Workup
- customThe mixture was partitioned between EtOAc (20 mL) and water (20 ml)
- washThe organic phase was washed with water (2×20 mL) and 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
Sources & evidence
- ORD record
- ord-e977cc0a97344407890f175b08eabeec
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087599B2
Linked notes
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