Sodium borohydride → Ethyl 2-fluorocyclopropanecarboxylate

HRID 130613

Reaktionsgleichung

Reaktionsgleichung von HRID 130613
[BH4-].[Na+].Cl[C:4]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH:5]1[F:7]>CN(C)C(=O)C.O.O.O.O.O.O.[Co](Cl)Cl>[F:7][CH:5]1[CH2:6][CH:4]1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 15346054Ethyl 1-chloro-2-fluorocyclopropanecarboxylate

Produkt 1

HCID 10313150Ethyl 2-fluorocyclopropanecarboxylateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 517166Dichlorocobalt hexahydrateKatalysatorHCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

Sodium borohydride (170 mg, 4.50 mmol) was added to and dissolved in N,N-dimethylacetamide (1.5 mL) at room temperature, followed by addition of an N,N-dimethylacetamide solution (1.0 mL) of ethyl 1-chloro-2-fluoro-cyclopropane-1-carboxylate (hereinafter the compound will be referred to as “compound (1b)”) (cis/trans=95/5) (500 mg, 3.00 mmol). Cobalt chloride hexahydrate (3.6 mg, 0.015 mmol) was added to the resultant solution at the same temperature. After completion of addition, the resultant mixture was stirred at 40° C. for one hour. After completion of reaction, the whole reaction mixture was diluted with an HPLC mobile phase to 50 mL, to thereby yield a solution containing 381.3 mg (yield: 96%) of the title compound. Yield was determined by means of high performance liquid chromatography (HPLC) (the same shall apply hereinafter).

Aufarbeitung

  1. additionAfter completion of addition
  2. customAfter completion of reaction
  3. customthe whole reaction mixture
  4. additionwas diluted with an HPLC mobile phase to 50 mL
  5. customto thereby yield a solution

Quellen und Nachweise

ORD-Eintrag
ord-e96fbc4c8237443aac969a665f78e102
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381833B2

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