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

HRID 538626노트

반응식

HRID 538626 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 5238Sodium Iodide촉매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

To 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 RT. 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 aq. 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%; ESI-MS: 161 [M+H]+

후처리

  1. additionAfter complete addition
  2. customThe reaction mixture is partitioned between TBME (3 L) and water (3 L)
  3. extractionthe aq. 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

출처 및 근거

ORD 기록
ord-b6c0326b5db24e7cb87ed512d00feaf8
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865744B1

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