Sodium hydride → Methyl 4-(4-(tert-butoxy)-3-(diethoxyphosphoryl)-4-oxobutan-2-yl)benzoate
Reaction equation
[H-].[Na+].[CH2:3]([O:5][P:6]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([O:8][CH2:9][CH3:10])=[O:7])[CH3:4].Br[CH:20]([C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)[CH3:21]>CN(C=O)C>[C:15]([O:14][C:12](=[O:13])[CH:11]([P:6]([O:5][CH2:3][CH3:4])([O:8][CH2:9][CH3:10])=[O:7])[CH:20]([C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)[CH3:21])([CH3:16])([CH3:18])[CH3:17]Participants
Conditions
- Temperature
- 0 °C
Procedure
Sodium hydride (60% dispersion in mineral oil, 2.98 g, 74.7 mmol) was added portionwise to a solution of tert-butyl 2-(diethoxyphosphoryl)acetate (12.6 g, 49.8 mmol) in anhydrous DMF (150 mL) at 23° C. over 20 min. The reaction mixture was cooled to 0° C., and then a solution of methyl 4-(1-bromoethyl)benzoate (12.1 g, 49.8 mmol) in anhydrous DMF (100 mL) was added dropwise over 15 min. The resulting mixture was stirred at room temperature for 5 h, then concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water (2×). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate in petrolum ethers to give the title compound. MS: m/z=829.4 (2M+1).
Workup
- concentrationconcentrated under reduced pressure
- customThe residue was partitioned between ethyl acetate and water (2×)
- washThe combined organic layers were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customThe residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate in petrolum ethers
Sources & evidence
- ORD record
- ord-998d4f48f4f746edacd85c9e1b97e3cf
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296750B2
Reaction notes
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