p-Toluenesulfonic acid → HCID 118023273, 화합물

HRID 522673노트

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HRID 522673 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:13])[CH2:11][OH:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].CO[C:16](OC)([CH3:18])[CH3:17].CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:17][C:16]1([CH3:18])[O:13][CH:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:11][O:12]1

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 41172001-(4-nitrophenyl)ethane-1,2-diol

생성물 1

HCID 118023273HCID 118023273, 화합물수율 46.8%

시약·촉매·용매 1

HCID 180Acetone용매

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온도
25 °C

실험 절차

A mixture of 1-(4-nitrophenyl)ethane-1,2-diol (7.0 g, 38.3 mmol), 2,2-dimethoxypropane (16 g, 153.2 mmol) and 4-methylbenzenesulfonic acid (2.6 g, 15.32 mmol) in acetone (100 mL) was stirred at 25° C. for 12 h. The reaction mixture was concentrated and then dissolved in ethyl acetate (300 mL). The organic layer was separated, washed by water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=5/1) to afford the title compound (4.0 g, 40%) as a yellow oil.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in ethyl acetate (300 mL)
  3. customThe organic layer was separated
  4. washwashed by water (100 mL) and brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-75456e14d3b24a13a9bd7dd04842bf38
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334263B2

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