Toluene → 3,4-dihydro-2H-thieno[3,4-b]thiopyran

HRID 576447Notes

Reaction equation

HRID 576447 reaction equation
CO[C:3]1[C:4]([CH2:8][CH2:9][CH2:10][SH:11])=[CH:5][S:6][CH:7]=1.O.S([O-])(O)(=O)=O.[Na+].C1(C)C=CC=CC=1>O>[S:11]1[CH2:10][CH2:9][CH2:8][C:4]2=[CH:5][S:6][CH:7]=[C:3]12

Participants

5

Reactant 3

HCID 1140TolueneHCID 23673662Sodium bisulfate monohydrateHCID 866649623-(4-Methoxythiophene-3-yl) propane-1-thiol

Product 1

HCID 596160473,4-dihydro-2H-thieno[3,4-b]thiopyranYield 82.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Into a 500 ml three-necked flask (reaction container) with thermometer, 2.47 g (13.1 mmol) of 3-(4-methoxythiophene-3-yl) propane-1-thiol represented by the chemical formula (III-B), 320 mg (2.32 mmol) of sodium hydrogen sulfate monohydrate and 100 ml of toluene were transferred and heated to 110° C., then stirred for a period of 8 hours. After the reaction was completed, 100 ml of water was added to separate the organic layer from the water layer. The organic layer was washed twice each with 100 ml of water, and then dried over anhydrous sodium sulfate. Then it was condensed under a reduced pressure, thereby obtaining a crude product. This crude product was purified using silica gel column chromatography to obtain 3,4-dihydro-2H-thieno[3,4-b]thiopyran (1.68 g, 10.8 mmol, 82.4%) represented by the formula (II-B) having properties shown below. The chemical reaction equation (XII-B) is shown below.

Workup

  1. customto separate the organic layer from the water layer
  2. washThe organic layer was washed twice each with 100 ml of water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customcondensed under a reduced pressure
  5. customobtaining a crude product
  6. customThis crude product was purified

Sources & evidence

ORD record
ord-b029b571f2154a2481923e7e749a6264
Source dataset
uspto-grants-2015_05
Patent number
US09039936B2

Reaction notes

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