Water → methyl (3R)-5-hydroxy-3-methylpentanoate
Reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][C@H:5]([CH3:10])[CH2:6][C:7](O)=[O:8].CSC.B.O>O1CCCC1>[CH3:10][C@H:5]([CH2:6][CH2:7][OH:8])[CH2:4][C:3]([O:2][CH3:1])=[O:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To 114 g. of 3-(R)-methylglutaric acid mono methyl ester in 715 ml. of dry tetrahydrofuran cooled to 0° C. was added slowly 391 ml. of 2M solution of borane dimethylsulfide in tetrahydrofuran. After the addition was complete the reaction mixture was stirred overnight at room temperature. The reaction was cooled and 50 ml. of water slowly added. The reaction was extracted (3×100 ml.) with ether and the extracts combined, washed with water, a saturated sodium bicarbonate solution and a brine solution, and dried over magnesium sulfate. Removal of the solvent gave 37 g. of the desired product.
Workup
- additionwas added slowly 391 ml
- additionAfter the addition
- temperatureThe reaction was cooled
- extractionThe reaction was extracted (3×100 ml.) with ether
- washwashed with water
- dry with materiala saturated sodium bicarbonate solution and a brine solution, and dried over magnesium sulfate
- customRemoval of the solvent
- customgave 37 g
Sources & evidence
- ORD record
- ord-88558ce846bc4845ad18af449473eb66
- Source dataset
- uspto-grants-1988_08
- Patent number
- US04767743
Reaction notes
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