3,4-dihydro-2H-pyran → Diethyl 5-(tetrahydropyran-2-yloxy)pentylphosphonate

HRID 2013

Reaction equation

HRID 2013 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10].[O:15]1[CH:20]=[CH:19][CH2:18][CH2:17][CH2:16]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[O:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][P:7](=[O:14])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10680635Diethyl 5-hydroxypentylphosphonate

Product 1

HCID 19689209Diethyl 5-(tetrahydropyran-2-yloxy)pentylphosphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 66.9 g (0.298 mol) of diethyl 5-hydroxypentylphosphonate, 32.6 g (0.38 mol) of 3,4-dihydropyran and 1 g (0.004 mol) of pyridinium toluene-4-sulfonate in 800 ml of dichloromethane was heated under reflux for 16 hours. The solution was washed with water and saturated sodium hydrogen carbonate solution, dried over sodium sulfate and distilled in a bulb tube.

Workup

  1. temperatureunder reflux for 16 hours
  2. washThe solution was washed with water and saturated sodium hydrogen carbonate solution
  3. dry with materialdried over sodium sulfate
  4. distillationdistilled in a bulb tube

Sources & evidence

ORD record
ord-1e24e4dd0b0641159e1602ba6f4a336e
Source dataset
uspto-grants-1998_03
Patent number
US05728686

Linked notes

Loading…