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

HRID 1051391Notes

Reaction equation

HRID 1051391 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9c2e21304cde435fb7c44d1c259b82cc
Source dataset
uspto-grants-2016_07
Patent number
US09388172B2

Reaction notes

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