Diethyl Ether → 3-(4-Benzyloxy-phenyl)-2-methyl-acrylic acid ethyl ester
Reaction equation
C([C:3](CC)(CC)[CH:4](P(O)(O)=O)[C:5]([O-:7])=[O:6])C.[H-].[Na+].[CH2:18]([O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:34](OCC)[CH3:35]>>[CH2:34]([O:7][C:5](=[O:6])[C:4]([CH3:3])=[CH:30][C:29]1[CH:32]=[CH:33][C:26]([O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:27][CH:28]=1)[CH3:35]Participants
Procedure
Triethyl-2-phosphonopropionate (22.2 mL, 103.65 mmol, d=1.111) is added to a 0° C. slurry of sodium hydride (4.15 g, 103.65 μmmol, 60% dispersion on mineral oil) in anhydrousTHF (150 mL), then allowed to warm to ambient temperature over thirty minutes. The slurry is re-cooled to 0° C. and 4-benzyloxybenzaldehyde (20 g, 94.23 mmol) is added in one portion as a solid. The reaction mixture is stirred 18 h at ambient temperature, then diluted with diethyl ether. The organic layer is washed with a saturated solution of aqueous ammonium chloride, water, and brine, then dried over MgSO4 and concentrated in vacuo. The residue is purified by flash chromatography to provide the title compound (24.3 g, 87%). 1H NMR (400 MHz, CDCl3): δ 7.67 (s, 1H), 7.46-7.35 (m, 6H), 7.01 (d, 2H, J=8.1 Hz), 5.10 (s, 2H), 4.28 (q, 2H, J=7.2 Hz), 2.15 (s, 3H), 1.36 (t, 3H, J=7.2 Hz). Rf=0.31 in 20% acetone in hexanes.
Workup
- temperatureThe slurry is re-cooled to 0° C.
- washThe organic layer is washed with a saturated solution of aqueous ammonium chloride, water, and brine
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe residue is purified by flash chromatography
Sources & evidence
- ORD record
- ord-0e1cd4f6c2244365b96ac1dcad725934
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07544812B2
Reaction notes
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