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

HRID 1243993ノート

反応式

HRID 1243993 の反応式
[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]

参加物

5

反応物 2

HCID 21004Methane, dichloromethoxy-HCID 21931845HCID 21931845、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dc181ac1db90483bbc6a6aec3246a431
出典データセット
uspto-grants-2006_10
特許番号
US07119207B2

反応ノート

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