2-Mercaptoethanol → HCID 15238320, compound

HRID 275284Notes

Reaction equation

HRID 275284 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8](S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.CC[O:30]CC>ClCCl>[O:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH:27]1[S:1][CH2:2][CH2:3][O:4][CH:8]1[CH2:9][CH2:10][CH2:5][CH2:15][O:30]1

Participants

6

Reactant 4

HCID 15672-MercaptoethanolHCID 3283Diethyl EtherHCID 80803,4-dihydro-2H-pyran2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 15238320HCID 15238320, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixed solution of 2-mercaptoethanol (25.0 g) and pyridinium p-toluenesulfonate (8.04 g) in dichloromethane (400 ml) was cooled with ice and 3,4-dihydro-2H-pyran (70 g) was gradually added. The mixture was stirred at room temperature for 3 hours. Then, 3,4-dihydro-2H-pyran (10.8 g) was further added and the mixture was stirred for an additional 3 hours. To this reaction mixture was added ether (1 l) and the organic layer was washed with aqueous sodium chloride solution and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The procedure gave 78.8 g of tetrahydropyran-2-yl 2-[(tetrahydropyran-2-yl)thio]ethyl ether as a colorless oil.

Workup

  1. additionwas gradually added
  2. stirringthe mixture was stirred for an additional 3 hours
  3. washthe organic layer was washed with aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-16bb0ae62e334fe9bc7f984dc7a43251
Source dataset
uspto-grants-1995_02
Patent number
US05393751

Reaction notes

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