Imidazole → 2,2-Dimethyl-3-triisopropylsilanyloxy-propionic acid methyl ester
Reaction equation
[CH3:1][C:2]([CH3:9])([CH2:7][OH:8])[C:3]([O:5][CH3:6])=[O:4].N1C=CN=C1.Cl[Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18]>C1COCC1.CN(C=O)C>[CH3:6][O:5][C:3](=[O:4])[C:2]([CH3:9])([CH3:1])[CH2:7][O:8][Si:16]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18]Participants
Procedure
To a solution of 6.76 mL (53 mmol) of methyl 2,2-dimethyl-3-hydroxypropionate in anhydrous THF/DMF (110 mL, 10/1) are added 4.33 g (63.6 mmol) of imidazole and 11.3 mL (53 mmol) of chlorotriisopropylsilane under nitrogen atmosphere. After stifling at room temperature for 20 h, the reaction mixture is concentrated under reduced pressure and the residue is dissolved in TBME (175 mL). The organic layer is washed with water (30 mL), brine (30 mL), dried over Na2SO4 and filtered. The filtrate is concentrated under reduced pressure to afford 13.25 g of 2,2-dimethyl-3-triisopropylsilanyloxy-propionic acid methyl ester as a yellow oil, which is used in the next step without further purification. Yield: 79%; 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.01-1.07 (21H, m), 1.18 (6H, s), 3.66 (3H, s), 3.69 (2H, s)
Workup
- concentrationthe reaction mixture is concentrated under reduced pressure
- dissolutionthe residue is dissolved in TBME (175 mL)
- washThe organic layer is washed with water (30 mL), brine (30 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationThe filtrate is concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b628f83a9da3464fa716912aa64f7b09
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08362039B2
Reaction notes
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