p-Toluenesulfonic acid → 2-Butyne, 1,4-bis[(tetrahydropyran-2-yl)oxy]-

HRID 1607815Notes

Reaction equation

HRID 1607815 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([OH:12])[C:8]#[C:9][CH2:10][OH:11].[C:13]1(C)C=[CH:17][C:16](S(O)(=O)=O)=[CH:15][CH:14]=1.C(N(CC)CC)C.[O:31]1CCCC1>>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:11][CH2:10][C:9]#[C:8][CH2:7][OH:12].[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:11][CH2:10][C:9]#[C:8][CH2:7][O:12][CH:17]1[CH2:16][CH2:15][CH2:14][CH2:13][O:31]1

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 80662-Butyne-1,4-diolHCID 80803,4-dihydro-2H-pyranHCID 8471Triethylamine

Product 2

HCID 5589232-Butyne, 1,4-bis[(tetrahydropyran-2-yl)oxy]-Yield 20%HCID 111233154-(Tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol

Conditions

Temperature
0 °C

Procedure

104.88 ml (96.69 g, 1.15 mol) of dihydropyran was added dropwise to a solution of 90 g (1.07 mol) of 2-butyn-1,4-diol and 9 g of p-toluenesulfonic acid in 1000 ml of tetrahydrofuran at such a rate to maintain the reaction temperature at 0° C. Thereafter the reaction mixture was stirred for 3 hours at room temperature. It was then neutralized with 10 ml of triethylamine and the solvent removed by evaporation in vacuo. The residue was purified by silica gel column chromatography using hexane:ethyl acetate (80:20) as eluant, to yield 2-butyne-1,4-diol monotetrahydropyranyl ether and 55.33 g (20%) of 2-butyne-1,4-diol bistetrahydropyranyl ether.

Workup

  1. customthe solvent removed by evaporation in vacuo
  2. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b6c4b23e68554419bf724b620b4494be
Source dataset
uspto-grants-1989_09
Patent number
US04867915

Reaction notes

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