Methane, dichloromethoxy- → 5-(1-Cyanocyclopropyl)-2-methoxybenzaldehyde

HRID 481485

반응식

HRID 481485 반응식
[C:1]([C:3]1([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[CH2:5][CH2:4]1)#[N:2].[CH3:14][O:15]C(Cl)Cl>ClCl.C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:1]([C:3]1([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([CH:7]=2)[CH:14]=[O:15])[CH2:5][CH2:4]1)#[N:2]

참가 물질

6

반응물 2

HCID 21004Methane, dichloromethoxy-HCID 855741-(4-Methoxyphenyl)cyclopropane-1-carbonitrile

생성물 1

HCID 190664325-(1-Cyanocyclopropyl)-2-methoxybenzaldehyde수율 88%

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매HCID 24526Chlorine용매

반응 조건

온도
-10 °C

실험 절차

To a stirred solution of Compound 1 (2.0 g, 11.6 mmol) in dry CH2 Cl2 (50 ml) was added TiCl4 (5.7 ml, 52.0 mmol) with cooling (-10° C.). After 15 min., to this was added a solution of dichloromethyl methyl ether (2.0 g, 17.3 mmol) in dry CH2Cl2 (5 ml) dropwise. The reaction mixture was stirred at same temperature for 10 min. and then at room temperature for 1 h. The mixture was poured into ice-water and stirred at room temperature for 15 min. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with brine, dried (MgSO4) and concentrated in vacuo to give crude product (2.36 g) as a yellow solid. The crude product was recrystallized from hexane-ethyl acetate to give Compound 2 (2.04 g, 88%) as a yellow solid.

후처리

  1. waitat room temperature for 1 h
  2. stirringstirred at room temperature for 15 min
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with CH2Cl2
  5. washThe combined solution was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give crude product (2.36 g) as a yellow solid
  9. customThe crude product was recrystallized from hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-18fbc390fd2f4696864d22583c4b9bb6
출처 데이터셋
uspto-grants-1998_08
특허 번호
US05789423

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