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

HRID 1051391ノート

反応式

HRID 1051391 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9c2e21304cde435fb7c44d1c259b82cc
出典データセット
uspto-grants-2016_07
特許番号
US09388172B2

反応ノート

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