Sodium Phosphate, Dibasic → 2-Isopropyl-3-methoxy-cyclohex-2-enone
Reaction equation
[CH:1]([CH:4]1[C:9]([O:10][CH3:11])=[CH:8][CH2:7][CH2:6][C:5]1=[O:12])([CH3:3])[CH3:2].C[O-].[Na+].P([O-])([O-])(O)=O.[Na+].[Na+]>C1COCC1>[CH:1]([C:4]1[C:5](=[O:12])[CH2:6][CH2:7][CH2:8][C:9]=1[O:10][CH3:11])([CH3:3])[CH3:2]Participants
Procedure
To a solution of 2-isopropyl-3-methoxy-cyclohex-3-enone (6 g) in dry THF (120 mL), sodium methoxide (1.5 g) was added in portions at room temperature. After stirring at room temperature for 1.5 hours, the reaction mixture was cooled in an ice bath and neutralized with 10% sodium hydrogen phosphate solution. The organic layer was separated, then the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine, then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the resulting product was purified on a column of silica gel (Hex:EtOAc) to give the title compound as a yellow liquid (5.4 g, 90%). 1H NMR (CDCl3): δ 1.09 (d, 6H, 2×CH3), 1.95 (m, 2H, CH2), 2.31 (t, 2H, CH2), 2.54 (t, 2H, CH2), 3.2 (m, 1H, CH), 3.78 (s, 3H, OCH3).
Workup
- temperaturethe reaction mixture was cooled in an ice bath
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
- washThe combined organic extracts were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was removed under reduced pressure
- customthe resulting product was purified on a column of silica gel (Hex:EtOAc)
Sources & evidence
- ORD record
- ord-4f305a024b5e40e584e7f58faa40e3a0
- Source dataset
- uspto-grants-2006_01
- Patent number
- US06982260B1
Reaction notes
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