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

HRID 481485

反応式

HRID 481485 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

HCID 190664325-(1-Cyanocyclopropyl)-2-methoxybenzaldehyde収率 88%

試薬・触媒・溶媒 3

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒HCID 24526Chlorine溶媒

反応条件

温度
-10 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-18fbc390fd2f4696864d22583c4b9bb6
出典データセット
uspto-grants-1998_08
特許番号
US05789423

関連ノート

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