2-O-Methyl-1,3-O,O-benzylideneglycerol → 1-O-benzyl-2-O-methylglycerol
Reaction equation
[C:1]1([CH:7]2[O:12][CH2:11][CH:10]([O:13][CH3:14])[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCCC1>[CH2:7]([O:8][CH2:9][CH:10]([O:13][CH3:14])[CH2:11][OH:12])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4.2 g of 2b was dissolved in 10 ml of tetrahydrofuran at 0° C. A solution of BH3 in tetrahydrofuran (1M, 30 ml) was added slowly, under stirring. Stirring was continued for 48 hours at room temperature. The mixture was then cooled to 0° C., quenched with cold water and extracted with diethyl ether. The solvent was eliminated and the crude product was chromatographed (eluent petroleum ether/diethyl ether, successively 80:20 and 70:30 by volume), yielding 2.6 g of 3b (62%).
Workup
- stirringStirring
- customquenched with cold water
- extractionextracted with diethyl ether
- customthe crude product was chromatographed (eluent petroleum ether/diethyl ether, successively 80:20 and 70:30 by volume),
Sources & evidence
- ORD record
- ord-93c70e656f0a483f9e464bdad4b45d31
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05116992
Reaction notes
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