Reaction equation
[H-].[Na+].Br[CH2:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1.C(OP(OCC)OCC)C.[CH:26](=O)[C:27]1[O:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[CH2:12]([O:11][C:9](=[O:10])[C:8]1[CH:14]=[CH:15][C:5](/[CH:4]=[CH:26]/[C:27]2[O:31][CH:30]=[CH:29][CH:28]=2)=[CH:6][CH:7]=1)[CH3:13]Participants
Procedure
60% Sodium hydride (0.48 g, 12 mmol) was suspended in anhydrous tetrahydrofuran (10 mL) under nitrogen atmosphere, and diethyl 4-ethoxycarbonyl benzylphosphonate (3.6 g, 12 mmol) prepared from ethyl 4-bromomethylbenzoate and triethylphosphite according to the methods as similar to those of Manufacturing Example 93-1-1 was added at room temperature and stirred for 30 minutes at room temperature. Furfural (1 g, 10.4 mmol) was then added at room temperature, and stirred for 2 hours at room temperature. The reaction mixture was partitioned into water and ethyl acetate on an ice bath (0° C.). The organic layer was washed with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:20) to obtain the title compound (1.07 g, 42%).
Workup
- additionwas added at room temperature
- stirringstirred for 2 hours at room temperature
- customThe reaction mixture was partitioned into water and ethyl acetate on an ice bath (0° C.)
- washThe organic layer was washed with water and saturated aqueous sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under a reduced pressure
- customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:20)
Sources & evidence
- ORD record
- ord-f348abe514fd4a04aa9597af93c161a3
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841327B2
Linked notes
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