Water → 4-Phenylthiobut-2-yn-1-ol tetrahydropyranyl ether

HRID 1607821Notes

Reaction equation

HRID 1607821 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:14][CH2:15][C:16]#[C:17][CH2:18]Br.O>C(O)C>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:14][CH2:15][C:16]#[C:17][CH2:18][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7969ThiophenolHCID 113682802-(4-Bromobut-2-ynoxy)tetrahydropyran

Product 1

HCID 198494564-Phenylthiobut-2-yn-1-ol tetrahydropyranyl ether

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of sodium ethoxide in ethanol, obtained from 1.3 g of sodium and 50 ml of absolute ethanol was treated dropwise with 5.5 g (0.05mol) of thiophenol in 15 ml of absolute ethanol. The reaction mixture was refluxed for 1 hour and then treated with 5.84 g (0.025 mol) of 1-bromobut-2-yn-4-ol tetrahydropyranyl ether, refluxing the mixture for 2 additional hours. It was then cooled, poured into water and extracted withmethylene chloride. The organic extract was washed with water, dried and evaporated to dryness in vacuo. The residue was purified by silica gel column chromatography, to produce 4-phenylthiobut-2-yn-1-ol tetrahydropyranyl ether, as an oil. Upon hydrolysis of the ether group with pyridinium p-toluenesulfonate in ethanol, in accordance with the method of Example 16, part E, there was obtained 4-phenylthiobut-2-yn-1-ol.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. temperaturerefluxing the mixture for 2 additional hours
  3. temperatureIt was then cooled
  4. extractionextracted withmethylene chloride
  5. extractionThe organic extract
  6. washwas washed with water
  7. customdried
  8. customevaporated to dryness in vacuo
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c30c3dcdff2842e4a3db8a4525cfd8a8
Source dataset
uspto-grants-1989_09
Patent number
US04867915

Reaction notes

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