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Ammonium Chloride → 2-[(4-Chloro-2-methoxyphenyl)(hydroxy)methyl]cyclopropanecarbonitrile

HRID 561487
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 561487
[BH4-].[Na+].[Cl: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])=[C:6]([O:17][CH3:18])[CH:5]=1.[Cl-].[NH4+]>C(O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:16]=[CH:15][C:7]([CH:8]([OH:9])[CH:10]2[CH2:12][CH:11]2[C:13]#[N:14])=[C:6]([O:17][CH3:18])[CH:5]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 583925482-(4-Chloro-2-methoxybenzoyl)cyclopropanecarbonitrile

Produkt 1

HCID 583921672-[(4-Chloro-2-methoxyphenyl)(hydroxy)methyl]cyclopropanecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

49.1 mg (1.30 mmol) of sodium borohydride were added to 278 mg (1.18 mmol) of the compound from Example 128A in 23 ml of ethanol and 10 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 1 h. The reaction mixture was added to saturated aqueous ammonium chloride solution and ethyl acetate, the phases were separated, the aqueous phase was extracted twice with ethyl acetate, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. 190 mg (68% of theory) of a mixture of the diastereomerse of the title compound were obtained.

Aufarbeitung

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialthe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. addition190 mg (68% of theory) of a mixture of the diastereomerse of the title compound
  7. customwere obtained

Quellen und Nachweise

ORD-Eintrag
ord-ba2998ad433c40a19f09f0b1407492c4
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08063234B2

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