Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonate → S-Tetrahydro-2H-pyran-4-YL ethanethioate

HRID 553594ノート

反応式

HRID 553594 の反応式
[O:1]1[CH2:6][CH2:5][CH:4](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:3][CH2:2]1.[C:18]([O-:21])(=[S:20])[CH3:19].[K+]>CN(C=O)C.[Na+].[I-]>[O:1]1[CH2:2][CH2:3][CH:4]([S:20][C:18](=[O:21])[CH3:19])[CH2:5][CH2:6]1

参加物

5

反応物 2

HCID 13961807Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonateHCID 23670855Potassium ethanethioate

生成物 1

HCID 18533108S-Tetrahydro-2H-pyran-4-YL ethanethioate収率 81.3%

試薬・触媒・溶媒 2

HCID 5238Sodium Iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 300 g (1.175 mol) of toluene-4-sulfonic acid tetrahydropyran-4-yl ester in DMF (3 L) are added 268 g (2.35 mol) potassium thioacetate, followed by a catalytic amount of NaI (0.12 g, 10 mol %) at room temperature. After complete addition, the reaction is heated to 50° C. for 20 h. The reaction mixture is partitioned between TBME (3 L) and water (3 L), the aqueous layer is extracted with TBME (2 L), then saturated with NaCl and extracted again with TBME (2×2 L). The combined organic extracts are dried over Na2SO4, filtered and the solvent is removed under reduced pressure to afford 153 g of thioacetic acid S-(tetrahydro-pyran-4-yl)ester. Yield: 81%; ES-MS: m/z 161 [M+H].

後処理

  1. additionAfter complete addition
  2. customThe reaction mixture is partitioned between TBME (3 L) and water (3 L)
  3. extractionthe aqueous layer is extracted with TBME (2 L)
  4. extractionsaturated with NaCl and extracted again with TBME (2×2 L)
  5. dry with materialThe combined organic extracts are dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-fed09d7da59d43999710ee5afc30b168
出典データセット
uspto-grants-2011_11
特許番号
US08048899B2

反応ノート

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