3,4-dihydro-2H-pyran → (2RS)-1-O-(2-Tetrahydropyranyl)-2-O-(5-methyl-3-isoxazolyl)glycerol

HRID 974697Notes

Reaction equation

HRID 974697 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([O:7][CH:8]([CH2:11][OH:12])[CH2:9][OH:10])[CH:3]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>C(Cl)Cl>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:10][CH2:9][CH:8]([CH2:11][OH:12])[O:7][C:4]1[CH:3]=[C:2]([CH3:1])[O:6][N:5]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 161440Pyridine 4-methylbenzene-1-sulfonateHCID 543308062-O-(5-Methyl-3-isoxazolyl)glycerol

Product 1

HCID 19986113(2RS)-1-O-(2-Tetrahydropyranyl)-2-O-(5-methyl-3-isoxazolyl)glycerol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 11.26 g of 2-O-(5-methyl-3-isoxazolyl)glycerol (prepared as described in Preparation 20), 5.93 ml of dihydropyran and 0.15 g of pyridine p-toluenesulfonate in 110 ml of methylene chloride was stirred at room temperature for 14 hours. The solvent was removed by evaporation under reduced pressure, and then the residue was subjected to column chromatography through 350 g of silica gel. 3.32 g of the 1,3-ditetrahydropyranyl compound was first eluted with a 1:4 by volume mixture of ethyl acetate and hexane, and then 9.67 g of the title compound were isolated as a colorless oil from the fractions eluted with a 1:1 by volume mixture of ethyl acetate and hexane.

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. wash3.32 g of the 1,3-ditetrahydropyranyl compound was first eluted with a 1:4 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-9252b55b22dc48548fe977536f2686ee
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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