Acetic Acid → 9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

A solution 2-butyl-4-chloro-5-methoxy-1-indanone (550 mg, 2.03 mmol) in tetrahydrofuran (4.06 mL) was treated with methyl vinyl ketone (0.203 mL, 2.44 mmol) and 0.5N sodium methoxide in methanol (0.812 mL, 0.406 mmol). The mixture was stirred at room temperature for 90 minutes to effect conversion to 2-butyl-4-chloro-5-methoxy-2-(3-oxobutyl)-1-indanone. The reaction mixture was evaporated under vacuum. The residue in toluene (10 mL) was treated with pyrrolidine (0.170 mL, 2.03 mmol) and acetic acid (0.140 mmol, 2.44 mmol). The resulting mixture was stirred and heated in an oil bath at 80° C. for 2.5 hours. After cooling to room temperature, the mixture was partitioned between EtOAc and water. The organic phase was washed with 0.1N HCl, saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by preparative layer chromatography on silica gel GF plates to afford 9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one.

1. customThe reaction mixture was evaporated under vacuum
2. stirringThe resulting mixture was stirred
3. temperatureheated in an oil bath at 80° C. for 2.5 hours
4. temperatureAfter cooling to room temperature
5. customthe mixture was partitioned between EtOAc and water
6. washThe organic phase was washed with 0.1N HCl, saturated aqueous NaHCO3 and brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customevaporated under vacuum
10. customThe residue was purified by preparative layer chromatography on silica gel GF plates

ORD-Eintrag

ord-5089406476cf406e8260118814d5a2c0

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07087599B2