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

HRID 652120Notes

Reaction equation

HRID 652120 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 (0.05 mol) 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 with methylene 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.

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 with methylene 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-9c8b696246314390aea24cf737314be1
Source dataset
uspto-grants-1987_06
Patent number
US04670465

Reaction notes

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