Dihydrobenzofuran → 2,3-Dihydrobenzofuran-5-carboxaldehyde

HRID 54572

반응식

HRID 54572 반응식
[CH3:1][O:2][CH:3](Cl)Cl.[O:6]1[C:10]2C=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7]1>C(Cl)Cl.CCOCC>[O:2]1[C:3]2[CH:7]=[CH:8][C:9]([CH:10]=[O:6])=[CH:14][C:13]=2[CH2:12][CH2:1]1

참가 물질

5

반응물 2

HCID 10329DihydrobenzofuranHCID 21004Methane, dichloromethoxy-

생성물 1

HCID 7359012,3-Dihydrobenzofuran-5-carboxaldehyde수율 60.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a stirred solution of α,α-dichloromethyl methyl ether (2.15 g, 19 mmol, 1.35 eq) in methylene chloride (30 mL) at -40° C. was added successively stannic chloride (1.65 g, 17 mmol, 1.2 eq) and 15 minutes later, a solution of 2,3-dihydrobenzofuran (1.68 g, 14 mmol) in CH2Cl2 (5 mL) maintaining the temperature at or below -35° C. The mixture was warmed to 0° C., stirred 1 hour, then poured into ice-water, and stirred a further 30 minutes. The mixture was diluted with ether, and the phases separated. The organic phase was concentrated in vacuo, and the residue purified by vacuum distillation to yield the title compound (1.25 g, 60%) as a colorless liquid. b.p. 119°-121° C. at 0.3 mm Hg.

후처리

  1. stirringstirred a further 30 minutes
  2. customthe phases separated
  3. concentrationThe organic phase was concentrated in vacuo
  4. distillationthe residue purified by vacuum distillation

출처 및 근거

ORD 기록
ord-aeae02a3858c4f9190646450ed5f9a61
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622971

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