Sodium Hydroxide → HCID 10784136、化合物

HRID 1734032ノート

反応式

HRID 1734032 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([N:7]([CH2:26][CH3:27])[CH2:8][CH2:9][N:10]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:14]3[S:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:12]([C:13]=23)=[N:11]1)[CH3:6].[CH3:28][O:29]C(Cl)Cl.[OH-].[Na+]>C(Cl)Cl.Cl.C(Cl)(Cl)Cl.O>[CH2:26]([N:7]([CH2:5][CH3:6])[CH2:8][CH2:9][N:10]1[C:18]2[CH:17]=[CH:16][C:15]([CH:28]=[O:29])=[C:14]3[S:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:12]([C:13]=23)=[N:11]1)[CH3:27]

参加物

9

反応物 4

HCID 14798Sodium HydroxideHCID 21004Methane, dichloromethoxy-HCID 6451240Aluminum(III) ChlorideHCID 10663709HCID 10663709、化合物

生成物 1

HCID 10784136HCID 10784136、化合物

試薬・触媒・溶媒 4

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

A suspension of aluminum chloride (1.76 g, 12.8 mmol) in CH2Cl2 (25 mL) is stirred at room temperature for 15 min and the compound of Example 1 (2.07 g, 6.38 mmol) in CH2Cl2 (15 mL) is added at 5° C. and the resulting mixture is stirred 10 min and cooled to 0° C. A solution of dichloromethyl methyl ether (1.52 g, 17.4 mmol) in 10 mL of CH2Cl2 is added dropwise over a period of 15 min. The mixture is allowed to warm to ambient temperature, stirred overnight and then diluted with of 2N HCl (10 mL) and cool water (100 mL). The mixture is poured into CHCl3 (100 mL), basified with 2N NaOH solution to pH 8-9 and the layers are separated. The aqueous layer is extracted with CHCl3 (40 mL). The combined organic layers are washed with water and dried over Na2SO4. Concentration and drying in vacuo gives crude aldehyde (2.16 g, 96%) which can be used without additional purification. The analytical sample is obtained by silica gel chromatography (EtOAc) following by recrystallization from EtOAc/hexane (1:2), mp: 81°-82.5° C. 1H NMR (CDCl3) 0.95 (6H; t), 2.54 (4H; q), 2.95 (2H; t), 4.40 (2H; t), 7.02 (1H; d), 7.23-7.40 (2H; m), 7.51-7.54 (1H; m), 7.64 (1H; d), 8.17-8.20 (1H; m), 10.02 (1H; s)ppm. MS m/z 352 (MH+). Anal. (C20H21N3OS) C, H, N.

後処理

  1. stirringthe resulting mixture is stirred 10 min
  2. temperaturecooled to 0° C
  3. temperatureto warm to ambient temperature
  4. stirringstirred overnight
  5. customthe layers are separated
  6. extractionThe aqueous layer is extracted with CHCl3 (40 mL)
  7. washThe combined organic layers are washed with water
  8. dry with materialdried over Na2SO4
  9. concentrationConcentration
  10. customdrying in vacuo
  11. customgives crude aldehyde (2.16 g, 96%) which
  12. customcan be used without additional purification
  13. customThe analytical sample is obtained by silica gel chromatography (EtOAc)
  14. customfollowing by recrystallization from EtOAc/hexane (1:2), mp: 81°-82.5° C

出典と根拠

ORDレコード
ord-38feefa51f49452b8fdc6df0bdfafa26
出典データセット
uspto-grants-1996_07
特許番号
US05532263

反応ノート

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