2-Butyne-1,4-diol → 4-(Tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol

HRID 2168

Reaction equation

HRID 2168 reaction equation
[CH2:1]([OH:6])[C:2]#[C:3][CH2:4][OH:5].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1>C1(C)C=CC(S(O)(=O)=O)=CC=1.CCOCC>[O:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[O:5][CH2:4][C:3]#[C:2][CH2:1][OH:6]

Participants

5

Reactant 2

HCID 80662-Butyne-1,4-diolHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 111233154-(Tetrahydro-pyran-2-yloxy)-but-2-yn-1-olYield 68.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic acid and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol.

Workup

  1. additionwas added dropwise
  2. customwas evaporated
  3. additionthe residue was poured into 200 ml of water
  4. extractionThe aqueous solution was extracted with hexane (2×100 ml)
  5. extractionre-extracted with ether (3×100 ml)
  6. washThe combined ether extracts were washed with 100 ml of brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-64ad41c7f6d34083816470ce8e3c45fd
Source dataset
uspto-grants-1998_03
Patent number
US05728715

Linked notes

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