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

HRID 442896ノート

反応式

HRID 442896 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([O:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([F:26])([F:25])[F:24])(=[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]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([F:25])([F:26])[F:24])(=[O:16])=[O:15])[CH:5]=[C:6]([CH:12]=1)[O:7][CH2:8][CH2:9][CH:10]=[O:11]

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 227224973-[5-Methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenoxy]propanol

生成物 1

HCID 227224873-[5-Methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenoxy]propionaldehyde収率 85.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Sulfur trioxide pyridine complex (1.12 mg, 7.0 mmol) was added to a solution of 3-[5-methyl-3-(2-trifluoromethylphenylsulfonyloxy)phenoxy]propanol (700 mg, 1.8 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 (50 mL). The mixture was extracted into dichloromethane (3×50 mL), then 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 (595 mg, 85%). 1H-NMR (300 MHz, CDCl3) δ 9.84 (s, 1 H), 8.13 (d, J=7.5 Hz, 1 H), 7.99 (d, J=7.5 Hz, 1 H), 7.80 (t, J=7.6 Hz, 1 H), 7.70 (t, J=7.3 Hz, 1 H), 6.62 (s, 1 H), 6.51 (s, 1 H), 6.45 (s, 1 H), 4.21 (t, J=6.0 Hz, 2 H), 2.87 (t, J=6.0 Hz, 2 H), 2.25 (s, 3 H).

後処理

  1. customquenched with 10% aqueous citric acid (50 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-67eb006cfc464870a83f4d1286937ee8
出典データセット
uspto-grants-1999_04
特許番号
US05891909

反応ノート

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