Dimethyl Sulfoxide → 3-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propionaldehyde

HRID 442929

반응식

HRID 442929 반응식
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:16][CH2:17][CH2:18][CH2:19][OH:20])(=[O:11])=[O:10])#[N:2].C(N(CC)C(C)C)(C)C.CS(C)=O>ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([O:12][C:13]1[CH:14]=[C:15]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[O:16][CH2:17][CH2:18][CH:19]=[O:20])(=[O:11])=[O:10])#[N:2]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 186697063-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propanol

생성물 1

HCID 227224093-[3-(2-Cyanophenylsulfonyloxy)-5-methylphenoxy]propionaldehyde수율 83.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Sulfur trioxide pyridine complex (480 mg, 3.0 mmol) was added to a solution of 3-[3-(2-cyanophenylsulfonyloxy)-5-methylphenoxy]propanol (315 mg, 0.9 mmol), as prepared in the preceding step, N,N-diisopropylethylamine (0.5 mL, 3.9 mmol) and anhydrous dimethyl sulfoxide (0.2 mL, 2.8 mmol) in anhydrous dichloromethane (10 mL). The reaction mixture was stirred at ambient temperature for 1 hour and then quenched with 10% aqueous citric acid (30 mL). The mixture was extracted into dichloromethane (3×40 mL), and the dichloromethane solution was washed with 10% aqueous citric acid (30 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 (260 mg, 83%). 1H-NMR (300 MHz, CDCl3) δ 9.84 (s, 1H), 8.11 (m, 1H), 7.94 (m, 1H), 7.78-7.81 (m, 2H), 6.65 (s, 1H), 6.61 (s, 1H), 6.57 (s, 1H), 4.24 (t, J=6.0 Hz, 2H), 2.88 (t, J=6.0 Hz, 2H), 2.27 (s, 3H).

후처리

  1. customquenched with 10% aqueous citric acid (30 mL)
  2. extractionThe mixture was extracted into dichloromethane (3×40 mL)
  3. washthe dichloromethane solution was washed with 10% aqueous citric acid (30 mL)
  4. dry with materialdried over Na2SO4
  5. customAfter removing the solvent in vacuo
  6. customthe residue was purified by flash column chromatography (dichloromethane)

출처 및 근거

ORD 기록
ord-b75a38a8c82c488299e6b949eded41fc
출처 데이터셋
uspto-grants-1999_04
특허 번호
US05891909

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