p-Toluenesulfonic acid → 2-(3-Butynyloxy)tetrahydro-2H-pyran

HRID 638131Notes

Reaction equation

HRID 638131 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1>CCOCC>[O:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH:22]1[O:5][CH2:1][CH2:2][C:3]#[CH:4]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 135663-Butyn-1-OL

Product 1

HCID 1424402-(3-Butynyloxy)tetrahydro-2H-pyranYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3-Butyn-1-ol (3) (7.0 g, 100 mmol) was dissolved in 50 mL dry ether, and the solution was cooled to 0°. A few crystals of p-toluenesulphonic acid were added, followed by dropwise addition of 9.24 g (110 mmol) of dihydropyran. The resulting solution was warmed to 20°, stirred for 16 hr, and extracted with saturated aqueous NaHCO3 (20 mL) and brine (20 mL). The solution was dried (MgSO4), concentrated in vacuo, and distilled to give 7 (14.78 g, 96% yield).

Workup

  1. temperaturethe solution was cooled to 0°
  2. temperatureThe resulting solution was warmed to 20°
  3. extractionextracted with saturated aqueous NaHCO3 (20 mL) and brine (20 mL)
  4. dry with materialThe solution was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. distillationdistilled

Sources & evidence

ORD record
ord-a67fb616361a454dba00b0f8ce039958
Source dataset
uspto-grants-1985_12
Patent number
US04560551

Reaction notes

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