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

HRID 7825

Reaction equation

[CH2:1]([C:5]1([CH2:17][CH2:18][C:19](=[O:22])[CH2:20][CH3:21])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[CH:11]=2)[C:6]1=O)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.Cl>[CH2:1]([C:5]12[CH2:17][CH2:18][C:19](=[O:22])[C:20]([CH3:21])=[C:6]1[C:7]1[C:12](=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=1)[CH2:13]2)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 2-butyl-5-methoxy-2-(3-oxo-pentyl)-1-indanone (84 mg, 0.28 mmol) in acetic acid (0.5 mL) and 6N HCl (0.5 mL) was stirred and heated in an oil bath at 100° C. for 21 hours. After cooling to room temperature, the reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL). The organic phase was washed with water (10 mL), 5% NaHCO3 (20 mL), and brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum to afford 9a-butyl-7-methoxy-4-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (76 mg) as a gum.

Workup

temperatureAfter cooling to room temperature
customthe reaction mixture was partitioned between EtOAc (20 mL) and water (20 mL)
washThe organic phase was washed with water (10 mL), 5% NaHCO3 (20 mL), and brine (10 mL)
dry with materialdried over MgSO4
filtrationfiltered
customevaporated under vacuum

Sources & evidence

ORD record: ord-13b6e50ba0aa46dbbb22df4807534675
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087599B2

Linked notes

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