p-Toluenesulfonic acid → 2-Methyl-3-butyn-2-yl 2-tetrahydropyranyl ether

HRID 622618Notes

Reaction equation

HRID 622618 reaction equation
[CH3:1][C:2]([OH:6])([CH3:5])[C:3]#[CH:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1>>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:6][C:2]([CH3:5])([CH3:1])[C:3]#[CH:4]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 82582-Methyl-3-butyn-2-ol

Product 1

HCID 41938432-Methyl-3-butyn-2-yl 2-tetrahydropyranyl ether

Procedure

3-Methyl-1-butyn-3-ol (25 ml, 21.7 g), dihydropyran (50 ml) and p-toluenesulphonic acid (5 mg) were mixed together at 0° C. for 1 hr, and then stirred at room temperature for a further 40 hr. The mixture was concentrated and the reside added to 5% aqueous NaHCO3 and extracted with benzene. The organic solution was dried to give after distillation 37.3 g (86%) of the title ether. b.p. 47° C./0.8 mm Hg (lit. 30°-33° C./ 0.5 mm50 ; 57° C./3.5mm170); 1Hnmr δ 5.6 (m, THP C-2'H), 2.45 (s. C-1H), 1.51 (s, CH3), 1.48 (s, CH3); IR (thin film) 3350 s), 2950 (s), 2900 (sh), 112S (s), 1070 (s), 1030 (s), cm-1.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe reside added to 5% aqueous NaHCO3
  3. extractionextracted with benzene
  4. customThe organic solution was dried
  5. customto give
  6. distillationafter distillation 37.3 g (86%) of the title ether
  7. customb.p. 47° C./0.8 mm Hg (lit. 30°-33° C./ 0.5 mm50 ; 57° C./3.5mm170)
  8. customIR (thin film) 3350 s

Sources & evidence

ORD record
ord-0b98fcf4ec7c41bfa489fc081d62ea3e
Source dataset
uspto-grants-1988_09
Patent number
US04772433

Reaction notes

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