Ethyl Acetate → S-[2-[4-[(Methylsulfonyl)oxy]phenyl]ethyl] ethanethioate

HRID 709442ノート

反応式

HRID 709442 の反応式
[C:1]([OH:4])(=[S:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].CS(O[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=1)(=O)=O.CCOC(C)=O>CO.CN(C=O)C.[Cl-].[Na+].O>[CH3:28][S:25]([O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][S:3][C:1](=[O:4])[CH3:2])=[CH:19][CH:20]=1)(=[O:27])=[O:26]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 112201221-(Methylsulfonyloxy)-2-[4-(methylsulfonyloxy)phenyl]ethaneHCID 178418634HCID 178418634、化合物2 回

生成物 1

HCID 86650296S-[2-[4-[(Methylsulfonyl)oxy]phenyl]ethyl] ethanethioate

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

Thioacetic acid (0.28 g, 3.73 mmol) was dissolved in anhydrous MeOH (3 mL) and Cs2CO3 (1.10 g, 3.39 mmol) was added. After 15 min. stirring at room temperature the MeOH evaporated under reduced pressure and the remaining oil was redissolved in anhydrous DMF (3 ml). Methanesulfonic acid 4-(2-methanesulfonyloxy-ethyl)-phenyl ester (1.00 g, 3.39 mmol), dissolved in anhydrous DMF (2 mL) was added dropwise and the reaction was stirred at room temperature for 4 h. Additional thioacetic acid (0.14 g, 1.86 mmol) was added to the reaction mixture. After 30 min. stirring, the mixture was partioned between EtOAc and brine. The separated organic layer was dried (Na2SO4) and finally concentration under reduced pressure. The crude material was purified by flash chromatography on silica gel 60 using n-heptan/EtOAc 7:3 as the eluent to afford the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 7.17-7.25 (m, 4H), 3.10 (s, 3H), 3.05-3.08 (t, 2H), 2.83-2.86 (t, 2H), 2.30 (s, 3H).

後処理

  1. customevaporated under reduced pressure
  2. dissolutionthe remaining oil was redissolved in anhydrous DMF (3 ml)
  3. additionwas added dropwise
  4. stirringAfter 30 min. stirring
  5. customThe separated organic layer was dried
  6. concentration(Na2SO4) and finally concentration under reduced pressure
  7. customThe crude material was purified by flash chromatography on silica gel 60 using n-heptan/EtOAc 7:3 as the eluent

出典と根拠

ORDレコード
ord-1d3135f0ac914551bda2237c4b896668
出典データセット
uspto-grants-2015_11
特許番号
US09181181B2

反応ノート

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