Triethylamine → 1,3-bis(benzyloxy)propan-2-yl Methacrylate
Reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:20])[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:32])[C:29]([CH3:31])=[CH2:30]>ClCCl>[C:28]([O:20][CH:10]([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:32])[C:29]([CH3:31])=[CH2:30]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
1,3-bis(benzyloxy)propan-2-ol (0.45 mL, 0.50 g, 1.8 mmol) and triethylamine (0.52 mL, 0.37 g, 3.7 mmol) were dissolved in dichloromethane and chilled to 0° C. Methacryloyl chloride (0.27 mL, 0.29 g, 2.8 mmol) was then added drop wise to the mixture. After mixing for 16 h, the mixture was then washed 100 mM pH 8.0 phosphate buffer (50 mL×3) and dried over anhydrous sodium sulfate. The solvent was subsequently removed using rotary evaporation under reduced pressure, and the product was isolated using silica gel chromatography at 81.0% yield.
Workup
- additionAfter mixing for 16 h
- washthe mixture was then washed 100 mM pH 8.0 phosphate buffer (50 mL×3)
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was subsequently removed
- customevaporation under reduced pressure
- customthe product was isolated
Sources & evidence
- ORD record
- ord-fc2c1d995ff649d2b074e4c025da86ce
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338492B2
Reaction notes
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