Tetrahydrofuran → HCID 89258928, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[O:11][CH2:12][O:13][CH3:14].O1CCCC1.C(OP([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])(OCC)=O)C.[H-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[CH:28]/[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:5][C:4]=1[O:11][CH2:12][O:13][CH3:14]Participants
6
Conditions
- Temperature
- 60 °C
Procedure
The compound (3.42 g, 17.4 mmol) of Example 9-1 was dissolved in N,N-dimethylformamide (30 ml) and tetrahydrofuran (30 ml) and then thereto were added ethyl diethylphosphonoacetate (3.91 g, 17.4 mmol) and sodium hydride (766 mg, 19.1 mmol). After stirring for 2 hours at 60° C., the mixture was allowed to cool to room temperature, and tetrahydrofuran was removed under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate-toluene (3:1). The organic layer was washed with water and an aqueous saturated sodium chloride solution in the order, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the subject compound (196 mg, 88.8%).
Workup
- temperatureto cool to room temperature
- customtetrahydrofuran was removed under reduced pressure
- additionTo the residue was added water
- extractionthe mixture was extracted with ethyl acetate-toluene (3:1)
- washThe organic layer was washed with water
- dry with materialan aqueous saturated sodium chloride solution in the order, dried over anhydrous magnesium sulfate
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-659f8461c0a04467bd73eade0b2eecef
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07220773B2
Reaction notes
Loading…