Trimethyl borate → Methyl 4-allyl-3-hydroxyoctanoate

Temperatur

70 °C

2-Allylhexanal (J. Org. Chem. 46, 1980, 5250) (5 g, 33.7 mmol), methyl bromoacetate (3.7 mL, 40 mmol), and zinc (2.6 g, 40 mmol) were added to tetrahydrofuran (30 mL) and trimethyl borate (15 mL), and the mixture was vigorously stirred. Then, the reaction vessel was placed in an oil bath and heated to 70° C., and the mixture was stirred for 2 hours. The mixture was allowed to cool, and glycerin (20 mL) and a saturated aqueous solution of ammonium chloride (100 mL) were then added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the compound of interest (diastereomeric mixture) as a colorless oil substance (6.8 g, 94%).

1. customThen, the reaction vessel was placed in an oil bath
2. stirringthe mixture was stirred for 2 hours
3. temperatureto cool
4. extractionfollowed by extraction with ethyl acetate
5. washThe organic layer was washed with water and saturated saline
6. dry with materialdried over anhydrous magnesium sulfate
7. distillationThen, the solvent was distilled off under reduced pressure
8. customthe residue was purified by silica gel column chromatography
9. customto obtain the compound of interest (diastereomeric mixture) as a colorless oil substance (6.8 g, 94%)

ORD-Eintrag

ord-7c96476fb6b641619f5e050b354b7014

Quelldatensatz

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07947738B2