Sulfuric Acid → Ethyl 4,4,4-trifluoro-3-(nitromethyl)butanoate

HRID 1051391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1051391
[F:1][C:2]([F:11])([F:10])/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6].[N+:12]([CH3:15])([O-:14])=[O:13].CN(C)C(=N)N(C)C.S(=O)(=O)(O)O>O>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][CH:3]([CH2:15][N+:12]([O-:14])=[O:13])[C:2]([F:10])([F:11])[F:1])[CH3:9]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 6375NitromethaneHCID 664601,1,3,3-TetramethylguanidineHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoate

Produkt 1

HCID 268363Ethyl 4,4,4-trifluoro-3-(nitromethyl)butanoateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4.203 g (25 mmol) of ethyl 4,4,4-trifluorocrotonate, 20 mL of nitromethane and ca 0.576 g (5 mmol) of tetramethyl guanidine were stirred for 13 hours at room temperature, and then diluted with water and acidified by the addition of 0.5 M sulfuric acid. The mixture was extracted three times with diethyl ether. The combined ether extracts were washed with water, and then brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 5.601 g (98%) of 4,4,4-trifluoro-3-nitromethyl-butyric acid ethyl ester as an amber oil.

Aufarbeitung

  1. extractionThe mixture was extracted three times with diethyl ether
  2. washThe combined ether extracts were washed with water
  3. dry with materialbrine, dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9c2e21304cde435fb7c44d1c259b82cc
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388172B2

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