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

HRID 553594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 553594
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 18533108S-Tetrahydro-2H-pyran-4-YL ethanethioateAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5238Sodium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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].

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fed09d7da59d43999710ee5afc30b168
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048899B2

Notizen zur Reaktion

Wird geladen…