Water → methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)octanoate

HRID 465625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 465625
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([CH2:20][CH:21]=[O:22])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([CH2:20][CH2:21][OH:22])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 10357812methyl (S)-8-(benzyloxy)-4-(formylmethyl)octanoate

Produkt 1

HCID 10380582methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)octanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of the crude methyl (S)-8-(benzyloxy)-4-(formylmethyl)octanoate (2.44 g crude) in ethanol (22 ml) is added sodium borohydride (0.307 g, 8.1 mmol). The reaction is stirred for 15 minutes and then poured into water. The pH of the mixture is adjusted to 8.0 using saturated sodium bicarbonate solution. The mixture is extracted with methylene chloride (3×30 ml) and the combined organic extracts are dried, filtered and evaporated to give an oil. This is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane as eluent to yield methyl (S)-8-(benzyloxy)-4-(2-hydroxyethyl)-octanoate (oil), [alpha]D25 -1.22° (c 1.02 in methanol).

Aufarbeitung

  1. extractionThe mixture is extracted with methylene chloride (3×30 ml)
  2. customthe combined organic extracts are dried
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil
  6. customThis is purified by flash chromatography on silica gel using 1:1 ethyl acetate/hexane as eluent

Quellen und Nachweise

ORD-Eintrag
ord-c34269d5450540fbb4a489cb196d0ddb
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153214

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