Methane, dichloromethoxy- → 6-Methoxy-3-methyl-2-oxo-1a,2,3,7b-tetrahydro-1H-3-aza-cyclopropa[a]naphthalene-5-carbaldehyde

HRID 1243993노트

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HRID 1243993 반응식
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]([CH3:15])[C:8](=[O:14])[CH:9]3[CH2:13][CH:10]32)=[CH:5][CH:4]=1.Cl[CH:17]([O:19]C)Cl>[Ti](Cl)(Cl)(Cl)Cl.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]([CH3:15])[C:8](=[O:14])[CH:9]3[CH2:13][CH:10]32)=[CH:5][C:4]=1[CH:17]=[O:19]

참가 물질

5

반응물 2

HCID 21004Methane, dichloromethoxy-HCID 21931845HCID 21931845, 화합물

생성물 1

HCID 99646446-Methoxy-3-methyl-2-oxo-1a,2,3,7b-tetrahydro-1H-3-aza-cyclopropa[a]naphthalene-5-carbaldehyde

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a flame dried round bottom flask equipped with a nitrogen cap was added 935 mg (4.6 mmol) 6-Methoxy-3-methyl-1,1a,3,7b-tetrahydro-3-aza-cyclopropa[a]naphthalen-2-one, and 40 ml of methylene chloride. The solution was cooled to 0° C. and 46.1 ml (46.1 mmol) of 1.0 M titanium tetrachloride was added. Dichloromethylmethylether (2.09 ml (23.05 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched in 100 ml ice/1N HCl. The aqueous phase was extracted with chloroform (3×30 ml). The combined organics were then washed with saturated bicarbonate solution and then brine followed by drying over sodium sulfate and evaporation in vacuo. The crude residue was taken up in ethyl acetate whereupon crystals formed. Four crops totaling 902 mg were obtained. Mass spectrum APCI m/e 232 (p+1).

후처리

  1. customTo a flame dried round bottom flask
  2. customequipped with a nitrogen
  3. customcap
  4. customThe reaction mixture was quenched in 100 ml ice/1N HCl
  5. extractionThe aqueous phase was extracted with chloroform (3×30 ml)
  6. washThe combined organics were then washed with saturated bicarbonate solution
  7. dry with materialby drying over sodium sulfate and evaporation in vacuo
  8. customformed
  9. customwere obtained

출처 및 근거

ORD 기록
ord-dc181ac1db90483bbc6a6aec3246a431
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07119207B2

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