Acetic Acid → 3-Oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester
Reaction equation
[C:1](=[O:6])([O:4][CH3:5])OC.[H-].[Na+].[CH2:9]1[C:14]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:13][CH2:12][C:11](=[O:20])[CH2:10]1.C(O)(=O)C>O1CCCC1.CC(C)([O-])C.[K+]>[CH3:5][O:4][C:1]([CH:12]1[C:11](=[O:20])[CH2:10][CH2:9][C:14]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:13]1)=[O:6]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
To a solution of dimethyl carbonate (17.9 g) in tetrahydrofuran (130 mL) were added 60% sodium hydride (9.9 g) and potassium tert-butoxide (0.14 g). To the mixture was added a solution of spiro[5.5]undecan-3-one (20.6 g) obtained in the same manner as in Step 2 in tetrahydrofuran (120 mL) at 85° C. over 2 hours, followed by stirring the reaction mixture at 85° C. for 1.5 hours. After cooling down to room temperature and adding 15% aqueous acetic acid solution (94.2 mL), the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried and concentrated to give 3-oxo-spiro[5.5]undecane-2-carboxylic acid methyl ester (29.6 g).
Workup
- temperatureAfter cooling down to room temperature
- extractionthe reaction mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-10248ee9b4d840a19ef84a09494555b5
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299296B2
Reaction notes
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