Sodium Bicarbonate → 4-(2H-1,3-Benzodioxol-4-yl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol

HRID 1444427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1444427
C([O:3][C:4](=O)[C:5]([OH:23])([C:19]([F:22])([F:21])[F:20])[CH2:6][C:7]([C:10]1[C:18]2[O:17][CH2:16][O:15][C:14]=2[CH:13]=[CH:12][CH:11]=1)([CH3:9])[CH3:8])C.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)(O)[O-].[Na+]>C(OCC)C>[O:15]1[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:7]([CH3:9])([CH3:8])[CH2:6][C:5]([C:19]([F:20])([F:22])[F:21])([OH:23])[CH2:4][OH:3])[C:18]=2[O:17][CH2:16]1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 17989248HCID 17989248, VerbindungHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 219488974-(2H-1,3-Benzodioxol-4-yl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diolAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

12.5 g (36.03 mmol) of 4-(1,3-benzodioxol-4-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)-pentanoic acid ethyl ester is introduced into 430 ml of diethyl ether and mixed in portions with 2.05 g (54.1 mmol) of lithium aluminum hydride at 0° C. After stirring overnight at room temperature, the batch is carefully added to sodium bicarbonate solution. It is filtered by means of diatomaceous earth and extracted three times with ethyl acetate. The combined organic extracts are washed with brine, dried, and the solvent is spun off after the desiccant is filtered off. Chromatography of the residue on silica gel (mobile solvent ethyl acetate/hexane) yields 6.7 g (61%) of the desired alcohol.

Aufarbeitung

  1. filtrationIt is filtered by means of diatomaceous earth
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic extracts are washed with brine
  4. customdried
  5. filtrationis filtered off

Quellen und Nachweise

ORD-Eintrag
ord-967a9662a573472ea96b6342215494b9
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662821B2

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