Ethanol → 1-Ethyl 3,3-difluoro-1,1-cyclobutanedicarboxylate

HRID 1497909ノート

反応式

HRID 1497909 の反応式
[F:1][C:2]1([F:16])[CH2:5][C:4]([C:11]([O:13]CC)=[O:12])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3]1.CCO>O>[CH2:9]([O:8][C:6]([C:4]1([C:11]([OH:13])=[O:12])[CH2:3][C:2]([F:1])([F:16])[CH2:5]1)=[O:7])[CH3:10]

参加物

4

反応物 2

HCID 702EthanolHCID 67231267Diethyl 3,3-difluorocyclobutane-1,1-dicarboxylate

生成物 1

HCID 672304401-Ethyl 3,3-difluoro-1,1-cyclobutanedicarboxylate

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

Diethyl 3,3-difluorocyclobutane-1,1-dicarboxylate (161) (2.8 g, 12 mmol) was dissolved in ice cooled ethanolic potassium hydroxide solution (0.5 M, 11 mL) and water (2.2 mL). The mixture was stirred at room temperature overnight. An additional 0.5 eq was added to the solution at room temperature and the mixture was stirred at room temperature overnight. Water was added and most of the EtOH was removed under reduced pressure. The mixture was acidified with 2M HCl and extracted three times with ethyl acetate. The organic layer was dried with magnesium sulfate and concentrated to yield 1-(ethoxycarbonyl)-3,3-difluorocyclobutanecarboxylic acid (162). 1H NMR (400 MHz, CD2Cl2) δ 4.33-4.24 (m, 2H), 3.26-3.13 (m, 4H), 1.34-1.27 (m, 3H). MS m/z 209.2 (M+1)+.

後処理

  1. additionAn additional 0.5 eq was added to the solution at room temperature
  2. stirringthe mixture was stirred at room temperature overnight
  3. customwas removed under reduced pressure
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-d7f057c27caf49dc90ab71670de6c5c5
出典データセット
uspto-grants-2015_12
特許番号
US09199981B2

反応ノート

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