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

HRID 481543ノート

反応式

HRID 481543 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

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
-60 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-eae49ffcc197424ab29aa825a399a947
出典データセット
uspto-grants-1998_08
特許番号
US05789423

反応ノート

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