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Dimethyl Sulfoxide → 3-[5-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenoxy]propionaldehyde

HRID 442949
ノート
印刷プレビュー

反応式

HRID 442949 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([O:13][S:14]([C:17]2[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=2[CH3:26])(=[O:16])=[O:15])[CH:5]=[C:6]([CH:12]=1)[O:7][CH2:8][CH2:9][CH2:10][OH:11].C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([O:13][S:14]([C:17]2[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=2[CH3:26])(=[O:16])=[O:15])[CH:5]=[C:6]([CH:12]=1)[O:7][CH2:8][CH2:9][CH:10]=[O:11]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 537902373-[5-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenoxy]propanol

生成物 1

HCID 543965433-[5-Methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenoxy]propionaldehyde収率 78%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Sulfur trioxide pyridine complex (960 mg, 6.0 mmol) was added to a solution of 3-[5-methyl-3-(2-methyl-5-nitrophenylsulfonyloxy)phenoxy]propanol (760 mg, 2.0 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.7 mL, 5.5 mmol) and anhydrous dimethyl sulfoxide (0.4 mL, 5.6 mmol) in anhydrous dichloromethane (20 mL). The reaction mixture was stirred at ambient temperature for 1 hour and then quenched with 10% aqueous citric acid (70 mL). The mixture was extracted into dichloromethane (3×50 mL), and the dichloromethane solution was washed with 10% aqueous citric acid (40 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane) to give the title compound as a colorless oil (590 mg, 78%). 1H-NMR (300 MHz, CDCl3) δ 9.83 (s, 1H), 8.72 (s, 1H), 8.38 (d, J=8.4 Hz, 1H), 7.63 (d, J=8.4 Hz, 1H), 6.63 (s, 1H), 6.46 (s, 1H), 6.39 (s, 1H), 4.21 (t, J=6.0 Hz, 2H), 2.89 (s, 3H), 2.87 (t, J=6.0 Hz, 2H), 2.26 (s, 3H).

後処理

  1. customquenched with 10% aqueous citric acid (70 mL)
  2. extractionThe mixture was extracted into dichloromethane (3×50 mL)
  3. washthe dichloromethane solution was washed with 10% aqueous citric acid (40 mL)
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvent in vacuo
  6. customthe residue was purified by flash column chromatography (dichloromethane)

出典と根拠

ORDレコード
ord-4e292a6dae364bf5b769d21922191eba
出典データセット
uspto-grants-1999_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05891909

反応ノート

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