Hydrochloric Acid → Methyl 5-phenyl-3,5-dihydroxypentanoate

HRID 2226275

Reaktionsgleichung

[C:1]1([CH:7]([OH:16])[CH2:8][C:9](=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([BH3-])#N.[Na+].O.Cl>CO.CC(C)[O-].CC(C)[O-].CC(C)[O-].[Cl-].[Ti+4]>[C:1]1([CH:7]([OH:16])[CH2:8][CH:9]([OH:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

1.03 g of methyl 5-phenyl-5-hydroxy-3-oxo-pentanoate is dissolved in 40 cm3 methanol. The solution is cooled to -10° C. and then 1.3 cm3 of 95% titanium chloride triisopropoxide (4.5 mmol) are added. The mixture is stirred for 20 minutes at -10° C. and then 329.6 mg of 95% sodium cyanoborohydride (50 mmol) are added. The mixture is stirred for 3 hours at a temperature between -5° and 0° C. 10 cm3 of water and 1 cm3 of concentrated hydrochloric acid are then added. After evaporation of the methanol under reduced pressure, the mixture is taken up in 70 cm3 of dichloromethane. The organic phase is washed with 2 times 50 cm3 of water and then dried over sodium sulphate. After filtration and concentration under reduced pressure, the product obtained is treated twice with methanol. There is thus obtained, with a yield of 70%, 720 mg of methyl 5-phenyl-3,5-dihydroxypentanoate for which the syn/anti ratio is equal to 93/7.

Aufarbeitung

stirringThe mixture is stirred for 3 hours at a temperature between -5° and 0° C
customAfter evaporation of the methanol under reduced pressure
washThe organic phase is washed with 2 times 50 cm3 of water
dry with materialdried over sodium sulphate
filtrationAfter filtration and concentration under reduced pressure
customthe product obtained

Quellen und Nachweise

ORD-Eintrag: ord-12c19bba2d87451cac8e7ff307c58b4f
Quelldatensatz: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05347039

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