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

HRID 1497909노트

반응식

HRID 1497909 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-d7f057c27caf49dc90ab71670de6c5c5
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199981B2

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