2-Butyl-4-chloro-5-methoxy-2-(3-oxopentyl)-1-indanone → 9a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 7856

Reaction equation

[CH2:1]([C:5]1([CH2:18][CH2:19][C:20](=[O:23])[CH2:21][CH3:22])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[C:11]=2[Cl:14])[C:6]1=O)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.Cl.CCOC(C)=O>[CH2:1]([C:5]12[CH2:18][CH2:19][C:20](=[O:23])[C:21]([CH3:22])=[C:6]1[C:7]1[C:12](=[C:11]([Cl:14])[C:10]([O:15][CH3:16])=[CH:9][CH:8]=1)[CH2:13]2)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 2-butyl-4-chloro-5-methoxy-2-(3-oxo-pentyl)-1-indanone (250 mg, 0.74 mmol) in acetic acid (2 mL) was diluted with 6N aqueous HCl (2 mL). The resulting mixture was stirred and heated in an oil bath at 90° C. for 18 hours, then kept at room temperature for 2 days. The mixture was diluted with EtOAc (20 mL), washed with water (30 mL), 5% NaHCO3 (10 mL) and brine (5 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil (250 mg). The crude product was purified by preparative layer chromatography on three 0.1×20×20 silica gel GF plates, developing with 5% EtOAc in CH2Cl2, to afford 9a-butyl-8-chloro-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (143 mg).

Workup

washwashed with water (30 mL), 5% NaHCO3 (10 mL) and brine (5 mL)
dry with materialdried over MgSO4
filtrationfiltered
customevaporated under vacuum to an oil (250 mg)
customThe crude product was purified by preparative layer chromatography on three 0.1×20×20 silica gel GF plates

Sources & evidence

ORD record: ord-6121252028114c99b582eb81c90945f8
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087599B2

Linked notes

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