Methanol → (R)-(-)-2-(1-Isobutoxyethoxy)-1-propanol

5.7 g of sodium borohydride was suspended at room temperature in a solution of 25.0 g of the isobutyl (R)-(+)-2-(1-isobutoxyethoxy)propionate (obtained in Reference Example 4) dissolved in 30 ml of cyclohexane. Thereto was dropwise added slowly 24 ml of methanol with stirring, so that the internal temperature of the reaction system could be kept at 40° C. After the completion of the dropwise addition, the mixture was stirred at room temperature for 5 hours. After the reaction, the reaction mixture was added 100 ml of water, followed by stirring for a while. Thereto was added 200 ml of ethyl acetate. The resulting organic layer was separated, washed with a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent. The resulting concentrate was subjected to distillation to obtain 17.3 g (yield: 98.0%) of an oily title compound (diastereomixture).

1. customcould be kept at 40° C
2. additionAfter the completion of the dropwise addition
3. stirringthe mixture was stirred at room temperature for 5 hours
4. customAfter the reaction
5. stirringby stirring for a while
6. customThe resulting organic layer was separated
7. washwashed with a saturated aqueous sodium chloride solution
8. dry with materialdried over anhydrous sodium sulfate
9. distillationThe resulting solution was subjected to vacuum distillation
10. customto remove the solvent
11. concentrationThe resulting concentrate
12. distillationwas subjected to distillation

ORD record

ord-a6e9fc21f40049389fa1e6c5bbb7c5ca

Source dataset

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06720463B1