3,4-dihydro-2H-pyran → 2-(4-Pentynyloxy)tetrahydro-2H-pyran

HRID 715961Notes

Reaction equation

HRID 715961 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([OH:12])[CH2:8][CH2:9][C:10]#[CH:11].C(=O)(O)[O-].[Na+]>CC1C=CC(S(O)(=O)=O)=CC=1>[CH2:7]([O:12][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1)[CH2:8][CH2:9][C:10]#[CH:11]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 793464-Pentyn-1-olHCID 516892Sodium Bicarbonate

Product 1

HCID 3578162-(4-Pentynyloxy)tetrahydro-2H-pyranYield 77.2%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

3,4-Dihydro-2H-pyran (5.0 g) was added dropwise to an ice cooled mixture of 4-pentyn-1-ol (5.0 g) and 4-methylbenzenesulfonic acid (0.512 g). The resultant mixture was stirred at room temperature for 4 hours. Solid sodium bicarbonate (1.0 g) was added and the mixture was stirred for 10 minutes, then filtered and washed with diethyl ether. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give 2-(pent-4-ynyloxy)tetrahydropyran (7.72 g) as a clear oil.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. washwashed with diethyl ether
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

Sources & evidence

ORD record
ord-3562ee54fdb14a73bf66059033640eed
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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