Ethanol → 2-[(Tetrahydropyran-2-yl)thio]ethanol

HRID 275285Notes

Reaction equation

HRID 275285 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[OH-:18].[Na+].[CH2:20]([OH:22])[CH3:21]>>[O:18]1[CH2:11][CH2:1][CH2:6][CH2:5][CH:4]1[S:7][CH2:21][CH2:20][OH:22]

Participants

4

Conditions

Temperature
55 °C

Procedure

To a solution of the compound of Reference Example 16 (78.8 g) in ethanol (1.5 ) was added pyridinium p-toluenesulfonate (8.04 g) and the mixture was stirred at 55° C. for 4 hours. To this reaction mixture was added 1N-NaOH (ca. 30 ml) and the solvent was distilled off under reduced pressure. To the residue was added ether (300 ml) and the suspension was dried over anhydrous sodium sulfate. The insolubles were filtered off and the filtrate was concentrated under reduced pressure. The residue was subjected to vacuum distillation to give 42.4 g of 2-[(tetrahydropyran-2-yl)thio]ethanol. bp 93°-94° C. /0.2 mmHg

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionTo the residue was added ether (300 ml)
  3. dry with materialthe suspension was dried over anhydrous sodium sulfate
  4. filtrationThe insolubles were filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. distillationThe residue was subjected to vacuum distillation

Sources & evidence

ORD record
ord-0e42747599d142dc80198d59ef837146
Source dataset
uspto-grants-1995_02
Patent number
US05393751

Reaction notes

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