3,4-dihydro-2H-pyran → HCID 18999663, compound

HRID 2260408Notes

Reaction equation

HRID 2260408 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>C(OCC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 223370184-(Bromomethyl)benzeneethanol

Product 1

HCID 18999663HCID 18999663, compoundYield 91.5%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 16.9 g (78.5 mmoles) of 4-(bromomethyl)benzeneethanol (prepared according to Plaue S. and Heissler D. Tetrahedron Lett. (1987) 28, 1401-4), 10.6 g (125 mmoles) of 3,4-dihydro-2H-pyrane and 0.16 g of para-toluenesulfonic acid in 160 ml dry ethyl ether, is stirred 16 hours at room temperature. The reaction mixture is thereafter washed with a solution saturated with sodium bicarbonate, then water, dried over Na2SO4 and concentrated, to give 21.5 g (yield=91.5%) of a yellow oil used without other purification.

Workup

  1. washThe reaction mixture is thereafter washed with a solution saturated with sodium bicarbonate
  2. dry with materialwater, dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ffb426f14b4542da8825fd0589bf05cf
Source dataset
uspto-grants-1995_12
Patent number
US05476846

Reaction notes

Loading…