Water → 2-Methoxy-5-[1-(1,3-dithiolan-2-yl)-1-methylethyl]benzaldehyde

HRID 481543

반응식

HRID 481543 반응식
[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)([CH:4]1[S:8][CH2:7][CH2:6][S:5]1)[CH3:3].[CH3:17][O:18]C(Cl)Cl.O>ClCl.C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:2]([CH:4]2[S:5][CH2:6][CH2:7][S:8]2)([CH3:1])[CH3:3])=[CH:10][C:11]=1[CH:17]=[O:18]

참가 물질

7

반응물 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 190664444-[1-Methyl-1-(1,3-dithiolan-2-yl)ethyl]anisole

생성물 1

HCID 190664902-Methoxy-5-[1-(1,3-dithiolan-2-yl)-1-methylethyl]benzaldehyde수율 30.5%

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매HCID 24526Chlorine용매

반응 조건

온도
-60 °C

실험 절차

To a stirred solution of Compound 80 (0.254 g, 1 mmol) in dry CH2 Cl2 (5 ml) was added a solution of TiCl4 in CH2Cl2 (1M, 3 ml) with cooling (-60° C.). After 3 min., to this was added dichloromethyl methyl ether (0.46 g, 4 mmol) dropwise. The reaction mixture was stirred at same temperature for 1 hr. The mixture was poured into water and stirred at room temperature for 15 min. The organic layer was separated and the aqueous layer was extracted with Et2O (50 ml×2). The combined solution was washed with brine, dried (MgSO4) and concentrated in vacuo to give crude product. The crude product was purified by a column chromatography to give Compound 81 (86 mg) as an oil

후처리

  1. stirringstirred at room temperature for 15 min
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with Et2O (50 ml×2)
  4. washThe combined solution was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give crude product
  8. customThe crude product was purified by a column chromatography

출처 및 근거

ORD 기록
ord-eae49ffcc197424ab29aa825a399a947
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789423

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