Sulfuric Acid → (3S)-3-(2-tetrahydropyranyloxy)-1-octyne

HRID 973336Notes

Reaction equation

HRID 973336 reaction equation
[CH:1]#[C:2][C@@H:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+]>>[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:9][C@@H:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:2]#[CH:1]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 80803,4-dihydro-2H-pyranHCID 10340Sodium CarbonateHCID 27345341-Octyn-3-ol, (3S)-

Product 1

HCID 11805967(3S)-3-(2-tetrahydropyranyloxy)-1-octyne

Procedure

A mixture of (3S)-1-octyn-3-ol (63 g., 0.5 mole) and dihydropyran (63 g., 0.75 mole) is cooled to 5° in an ice bath and stirred while concentrated sulfuric acid (0.5 ml.) is added dropwise. The resulting solution is allowed to warm to room temperature and stand for 24 hours. The solution is then treated with solid anhydrous sodium carbonate, filtered, and distilled to yield (3S)-3-(2-tetrahydropyranyloxy)-1-octyne.

Workup

  1. temperatureis cooled to 5° in an ice bath
  2. additionis added dropwise
  3. filtrationfiltered
  4. distillationdistilled

Sources & evidence

ORD record
ord-22e5bcc0625f4f3d8969f8b99657e10d
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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