Sodium hydride → methyl 8-oxo-1,4-dioxaspiro[4.5]decane-7-carboxylate
Reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[O:3][CH2:2]1.[H-].[Na+]>C(=O)(OC)OC.C1(C)C=CC=CC=1>[O:10]=[C:7]1[CH2:6][CH2:5][C:4]2([O:3][CH2:2][CH2:1][O:11]2)[CH2:9][CH:8]1[C:4]([O:3][CH3:2])=[O:11]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of 1,4-cyclohexanedione monoethylene ketal (1.00 g, 6.4 mmol) in dimethyl carbonate (6 mL) at room temperature was added sodium hydride (0.31 g, 7.7 mmol). The mixture was heated at 80° C. for 20 min and then diluted with dry toluene (20 mL). The mixture was stirred for an additional 3 h at 80° C., cooled to room temperature, quenched with water, and then extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate and evaporated to yield the crude product which was purified by Biotage® chromatography (silica gel, ethyl acetate in hexanes gradient 30-42%) to yield the title compound.
Workup
- temperaturecooled to room temperature
- customquenched with water
- extractionextracted with dichloromethane
- dry with materialThe organic phase was dried over anhydrous sodium sulfate
- customevaporated
- customto yield the crude product which
- customwas purified by Biotage® chromatography (silica gel, ethyl acetate in hexanes gradient 30-42%)
Sources & evidence
- ORD record
- ord-7ecbbe6a01a847fea1215bc9e9daabe5
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482336B2
Reaction notes
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