Water → 2-[Hydroxy(4-methylphenyl)methyl]cyclopropanecarbonitrile

HRID 561482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 561482
[BH4-].[Na+].[CH3:3][C:4]1[CH:16]=[CH:15][C:7]([C:8]([CH:10]2[CH2:12][CH:11]2[C:13]#[N:14])=[O:9])=[CH:6][CH:5]=1.O>C(O)C.C(OCC)(=O)C>[OH:9][CH:8]([C:7]1[CH:6]=[CH:5][C:4]([CH3:3])=[CH:16][CH:15]=1)[CH:10]1[CH2:12][CH:11]1[C:13]#[N:14]

Komponenten

6

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 583924152-(4-Methylbenzoyl)cyclopropanecarbonitrile

Produkt 1

HCID 583923442-[Hydroxy(4-methylphenyl)methyl]cyclopropanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

607 mg (16.0 mmol) of sodium borohydride were added to 2.70 g (14.6 mmol) of the compound from Example 126A in 60 ml of ethanol and 16 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 2 h. The reaction mixture was added to water and extracted with dichloromethane, and the organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) to result in 2.56 g (94% of theory) of a mixture of the diastereomers of the title compound.

Aufarbeitung

  1. extractionextracted with dichloromethane
  2. washthe organic phase was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-813536802ef449fca12bbcf7d7b84346
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

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