p-Toluenesulfonic acid → HCID 118023273、化合物

HRID 522673ノート

反応式

HRID 522673 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 118023273HCID 118023273、化合物収率 46.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-75456e14d3b24a13a9bd7dd04842bf38
出典データセット
uspto-grants-2016_05
特許番号
US09334263B2

反応ノート

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