Methanol → 13-Methyl-1,8,11,12,13,14,15,16-octahydro-2H,6H-7-oxa-cyclopenta[a]phenanthrene-3,17-dione
Reaction equation
C[O-].[Na+].CO.[CH3:6][C:7]12[C:25](=[O:26])[CH2:24][CH2:23][CH:8]1[CH:9]1[C:14]([CH2:15][CH2:16]2)=[C:13]([CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[C:12](=O)[CH2:11][O:10]1>C1(C)C=CC=CC=1>[CH3:6][C:7]12[CH2:16][CH2:15][C:14]3[CH:9]([O:10][CH2:11][C:12]4[C:13]=3[CH2:17][CH2:18][C:19](=[O:21])[CH:20]=4)[CH:8]1[CH2:23][CH2:24][C:25]2=[O:26]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A 25% (w/w) solution of sodium methoxide in methanol (2.71 mL, 12.8 mmol, 1 eq) was added to a stirred solution of the crude 3a-Methyl-6-(3-oxo-butyl)-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione in toluene (200 mL) at 0° C. The resulting mixture was stirred at 0° C. for 0.5 h. The reaction was then quenched with a 10:1 (v/v) of ammonium chloride/potassium bisulfate solution (100 mL). The aqueous layer was extracted with ethyl acetate (2×100 mL), and the combined organic layer was dried with magnesium sulfate. The resulting solution was filtered, evaporated and the residue purified by flash chromatography using 30-50% ethyl acetate in hexane to yield the title compound as a white solid.
Workup
- customThe reaction was then quenched with a 10:1 (v/v) of ammonium chloride/potassium bisulfate solution (100 mL)
- extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
- dry with materialthe combined organic layer was dried with magnesium sulfate
- filtrationThe resulting solution was filtered
- customevaporated
- customthe residue purified by flash chromatography
Sources & evidence
- ORD record
- ord-248325029a0e45e9bc1fd0bb91f7f565
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763648B2
Reaction notes
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