3,4-dihydro-2H-pyran → 1-Pentanol, 5-[(tetrahydro-2H-pyran-2-yl)oxy]-

HRID 2371554Notes

Reaction equation

HRID 2371554 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1>C1(C)C=CC(S(=O)=O)=CC=1.C(Cl)(Cl)Cl>[OH:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][O:7][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][O:8]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 81051,5-Pentanediol

Product 1

HCID 5590981-Pentanol, 5-[(tetrahydro-2H-pyran-2-yl)oxy]-Yield 31.9%

Reagents, catalysts & solvents 2

HCID 178427284HCID 178427284, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To 31.2 g of 1.5-pentanediol was added 380 mg of p-toluenesulfonic acid monohydride and dropwise 8.4 g of dihydropyran with ice-cooling and stirring over 20 minutes, and the mixture was stirred at a room temperature for 3.5 hours. After adding 300 ml of chloroform, the mixture was washed with 2% sodium bicarbonate aqueous solution, water and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, filtered and evaporated under a reduced pressure. The residue was applied to a silica gel column and eluted with hexane/ethyl acetate (3:1) to obtain 6.0 g of 2-(5-hydroxypentyloxy)tetrahydropyran as a colorless liquid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at a room temperature for 3.5 hours
  3. washthe mixture was washed with 2% sodium bicarbonate aqueous solution, water
  4. dry with materiala saturated sodium chloride aqueous solution, dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under a reduced pressure
  7. washeluted with hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-f8a670b228ca4df0a629326be80c15f4
Source dataset
uspto-grants-1992_03
Patent number
US05093370

Reaction notes

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