p-Toluenesulfonic acid → Ethyl ({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate

HRID 603914ノート

反応式

HRID 603914 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:19])[CH2:11][S:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:20][C:21]([CH3:26])([CH2:24]O)[CH2:22][OH:23].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:11][S:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:23][CH2:22][C:21]([CH3:26])([CH3:24])[CH2:20][O:19]3)=[CH:9][C:4]=2[O:3][CH2:2]1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 31344Neopentyl glycolHCID 43218502Ethyl {[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]thio}acetate

生成物 1

HCID 59197900Ethyl ({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)acetate

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

Ethyl {[2-(1,3-benzodioxol-5-yl)-2-oxoethyl]thio}acetate (Method 11) (15.8 g, 0.056 mol) was dissolved in benzene (500 mL) and 2,2-dimethyl-1,3-propanediol (46.6 g, 0.45 mol) and p-toluene sulfonic acid (cat., 500 mg) were added. The mixture was stirred at reflux in a Dean-Stark apparatus for two hours, given room temperature and concentrated under reduced pressure. The resulting white solid was dissolved in CH2Cl2 (500 mL) and washed twice with water (300 mL) and brine (300 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude oil was purified by flash-chromatography (heptane:EtOAc 4:1) to afford the desired product.

後処理

  1. temperatureat reflux in a Dean-Stark apparatus for two hours
  2. customgiven room temperature
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting white solid was dissolved in CH2Cl2 (500 mL)
  5. washwashed twice with water (300 mL) and brine (300 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude oil was purified by flash-chromatography (heptane:EtOAc 4:1)

出典と根拠

ORDレコード
ord-362fb4240c71418a80d80f86e22d65ba
出典データセット
uspto-grants-2011_03
特許番号
US07906502B2

反応ノート

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