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Diethyl Ether → (4-Chlorophenyl)(2,2-difluorocyclopropyl)methanol

HRID 561483
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 561483
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH:12]2[CH2:14][C:13]2([F:16])[F:15])=[O:11])=[CH:6][CH:5]=1.[Cl-].[NH4+].C(OCC)C>C(O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([CH:12]2[CH2:14][C:13]2([F:15])[F:16])[OH:11])=[CH:8][CH:9]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 248658712,2-Difluorocyclopropyl(4-chlorophenyl) ketone

Produkt 1

HCID 58392413(4-Chlorophenyl)(2,2-difluorocyclopropyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702
Ethanol
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

336 mg (8.89 mmol) of sodium borohydride were added to 1.75 g (8.08 mmol) of the compound from Example 124A in 33 ml of ethanol and 9 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 diethyl ether, the phases were separated, the aqueous phase was extracted twice with diethyl ether, and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. 1.44 g (82% of theory) of a mixture of the diastereomers of the title compound were obtained.

Aufarbeitung

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted twice with diethyl ether
  3. washthe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. addition1.44 g (82% of theory) of a mixture of the diastereomers of the title compound
  8. customwere obtained

Quellen und Nachweise

ORD-Eintrag
ord-fc5f375805a94fe8af6a928964fd7edd
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08063234B2

Notizen zur Reaktion

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