Hydrochloric Acid → Methyl 2-tert-butoxycarbonyl-1-chloro-1-cyclopropanecarboxylate

HRID 1956826

Reaktionsgleichung

Reaktionsgleichung von HRID 1956826
[H-].[Na+].[C:3]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[CH:4]=[CH2:5].[Cl:12][CH:13](Cl)[C:14]([O:16][CH3:17])=[O:15].Cl>CN(C)C=O.O>[C:8]([O:7][C:3]([CH:4]1[CH2:5][C:13]1([Cl:12])[C:14]([O:16][CH3:17])=[O:15])=[O:6])([CH3:11])([CH3:10])[CH3:9]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8315Methyl dichloroacetateHCID 15458tert-Butyl acrylateHCID 24758Sodium hydride

Produkt 1

HCID 10014285Methyl 2-tert-butoxycarbonyl-1-chloro-1-cyclopropanecarboxylateAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

80 g of 60% sodium hydride was suspended in 1,000 ml of N,N-dimethylformamide. To this suspension was dropped 352 ml of tert-butyl acrylate within 30 minutes under ice-cooling. Then 207 ml of methyl dichloroacetate was dropped into this reaction mixture within 1.5 hours while maintaining the internal temperature at 10° C. After the completion of the addition, the mixture was stirred for 2 hours while maintaining the internal temperature at 10° to 20° C. Then the reaction mixture was neutralized by adding concentrated hydrochloric acid and water was-further added thereto. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with a saturated aqueous solution of sodium chloride. The extract was dried over anhydrous sodium sulfate and then the solvent was evaporated under reduced pressure. The obtained residue was distilled under reduced pressure to thereby give 384 g (yield 84%) of methyl 2-tert-butoxycarbonyl-1-chloro-1-cyclopropanecarboxylate in the form of a colorless oily product.

Aufarbeitung

  1. temperaturecooling
  2. additionAfter the completion of the addition
  3. temperaturewhile maintaining the internal temperature at 10° to 20° C
  4. additionwas-further added
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. distillationThe obtained residue was distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-acfe2c0dd7c04502ac76248e379b1f73
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05780669

Verknüpfte Notizen

Wird geladen…