p-Toluenesulfonic acid → 2-[(Hept-6-yn-2-yl)oxy]oxane

HRID 638130Notes

Reaction equation

HRID 638130 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH:6]([OH:8])[CH3:7].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1>CCOCC>[O:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[O:8][CH:6]([CH3:7])[CH2:5][CH2:4][CH2:3][C:2]#[CH:1]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 133371736-Heptyn-2-ol

Product 1

HCID 133371742-[(Hept-6-yn-2-yl)oxy]oxaneYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Alcohol 5 (7.7 g, 68.75 mmol) was dissolved in 75 mL dry ether and cooled to 0°. A few crystals of p-toluenesulphonic acid were added, followed by dropwise addition of 6.35 g (75.6 mmol) of dihydropyran. The solution was warmed to 20°, stirred for 18 hr, and then extracted with saturated aqueous NaHCO3 (25 mL) and brine (25 mL). The solution was dried (MgSO4), concentrated in vacuo, and distilled, yielding 12.96 g of 6 (96% yield).

Workup

  1. temperaturecooled to 0°
  2. temperatureThe solution was warmed to 20°
  3. extractionextracted with saturated aqueous NaHCO3 (25 mL) and brine (25 mL)
  4. dry with materialThe solution was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. distillationdistilled

Sources & evidence

ORD record
ord-f82b737cfc7e458b8036090eda5ebc7a
Source dataset
uspto-grants-1985_12
Patent number
US04560551

Reaction notes

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