Diazomethane → Ethyl 2-(3-fluoro-4-methoxyphenyl)cyclopropanecarboxylate

HRID 445815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445815
CN(N=O)C(N[N+]([O-])=O)=N.[OH-].[K+].[N+](=[CH2:15])=[N-].[F:16][C:17]1[CH:18]=[C:19](/[CH:25]=[CH:26]/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]>CCOCC.C(O)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:16][C:17]1[CH:18]=[C:19]([CH:25]2[CH2:15][CH:26]2[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Komponenten

8

Edukt 4

HCID 9550Diazomethane3×HCID 14797Potassium HydroxideHCID 12330260HCID 12330260, VerbindungHCID 135436526N-Methyl-N'-nitro-N-nitrosoguanidine

Produkt 1

HCID 58566289Ethyl 2-(3-fluoro-4-methoxyphenyl)cyclopropanecarboxylateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 167845palladium(II) acetateKatalysator2×HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a mixture of N-methyl-N′-nitro-N-nitrosoguanidine (TCI-America catalogue #M0527, 3.7 g on a dry weight basis, 25.0 mmol) in ether (50 mL) at 0° C. was added a cold solution of 25% aqueous KOH (20 mL). After stirring for 2 minutes, a portion of the yellow ethereal solution of the resulting diazomethane was added to a solution of the alkene (537) (1.1 g, 5.0 mmol) in ether (25 mL) at 0° C. A portion of palladium (II) acetate (0.112 g, 0.50 mmol) was added followed by an additional portion of diazomethane solution. This process was continued until all the diazomethane solution and palladium (II) acetate was added. The resulting mixture was stirred at 0-5° C. for 4 hours and acetic acid (6 drops) was added to quench any excess reagent. The resulting mixture was concentrated in vacuo to provide ethyl 2-(3-fluoro-4-methoxyphenyl)cyclopropane carboxylate (538) (0.990 g, 83.0%) as a yellow oil.

Aufarbeitung

  1. additionwas added
  2. stirringThe resulting mixture was stirred at 0-5° C. for 4 hours
  3. customto quench any excess reagent
  4. concentrationThe resulting mixture was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c8dc72e7929d4255a026aa9de346087f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476308B2

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