Ethanol → Diethyl 5-hydroxy-1,1-dimethylpentylphosphonate

HRID 2015

Reaction equation

HRID 2015 reaction equation
CC(C)CCCC([P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])OC1CCCCO1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26](S([O-])(=O)=O)=[CH:25][CH:24]=1.[NH+]1C=CC=CC=1.C([OH:42])C>>[OH:42][CH2:25][CH2:26][CH2:27][CH2:28][C:23]([P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17])([CH3:24])[CH3:33]

Participants

4

Reactant 3

HCID 702EthanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 19689172Diethyl 1,1-dimethyl-5-(tetrahydropyran-2-yloxy)-5-pentylphosphonate

Product 1

HCID 19689221Diethyl 5-hydroxy-1,1-dimethylpentylphosphonate

Procedure

19.9 g (0.052 mol) of diethyl 1,1-dimethyl-5-(tetrahydropyran-2-yloxy)-5-pentylphosphonate were stirred at 55° C. for 8 hours with 1.5 g (0.006 mol) of pyridinium toluene-4-sulfonate in 200 ml of aqueous ethanol. The solvent was evaporated, the residue was taken up in ethyl acetate, the solution was filtered through a silica gel column and, after evaporating the solvent, the residue was distilled in a bulb tube.

Workup

  1. customThe solvent was evaporated
  2. filtrationthe solution was filtered through a silica gel column
  3. customafter evaporating the solvent
  4. distillationthe residue was distilled in a bulb tube

Sources & evidence

ORD record
ord-73eb847fa4744d04af4bf241c54b60cc
Source dataset
uspto-grants-1998_03
Patent number
US05728686

Linked notes

Loading…