Methanol → 3a-Methyl-6-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-1,2,4,5,9a,9b-hexahydro-3aH-9-oxa-cyclopenta[a]naphthalene-3,7-dione
Reaction equation
C[O-].[Na+].CO.[CH3:6][C:7]12[C:15](=[O:16])[CH2:14][CH2:13][CH:12]1[CH:11]([O:17][CH2:18][C:19](=[O:29])[CH2:20][CH2:21][CH2:22][C:23]1([CH3:28])[O:27][CH2:26][CH2:25][O:24]1)[C:10](=O)[CH2:9][CH2:8]2>C1(C)C=CC=CC=1>[CH3:6][C:7]12[C:15](=[O:16])[CH2:14][CH2:13][CH:12]1[CH:11]1[C:10]([CH2:9][CH2:8]2)=[C:20]([CH2:21][CH2:22][C:23]2([CH3:28])[O:27][CH2:26][CH2:25][O:24]2)[C:19](=[O:29])[CH2:18][O:17]1Participants
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 the stirred solution of 7a-Methyl-4-[5-(2-methyl-[1,3]dioxolan-2-yl)-2-oxo-pentyloxy]-hexahydro-indene-1,5-dione (4.5 g, 12.8 mmol, 1 eq) in toluene (200 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h, then the reaction was 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 then filtered and concentrated to yield the title compound as an oil, which was used in the next step without further purification.
Workup
- customthe reaction was 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 then filtered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-93cac694a7e04e3b8f88cb9ce2d4fbbb
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763648B2
Reaction notes
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