Ethanol → 2-[(Tetrahydropyran-2-yl)thio]ethanol
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
- distillationthe solvent was distilled off under reduced pressure
- additionTo the residue was added ether (300 ml)
- dry with materialthe suspension was dried over anhydrous sodium sulfate
- filtrationThe insolubles were filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- 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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