Potassium Carbonate → 3-[4-(3-Hydroxybutoxy)phenyl]-5-methoxymethyl-2-oxazolidinone

HRID 1681359Notes

Reaction equation

HRID 1681359 reaction equation
S(O[CH2:12][CH2:13][CH:14]([OH:16])[CH3:15])(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[OH:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:34][CH:33]([CH2:35][O:36][CH3:37])[O:32][C:31]2=[O:38])=[CH:26][CH:25]=1>CC(CC)=O>[OH:16][CH:14]([CH3:15])[CH2:13][CH2:12][O:23][C:24]1[CH:25]=[CH:26][C:27]([N:30]2[CH2:34][CH:33]([CH2:35][O:36][CH3:37])[O:32][C:31]2=[O:38])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 131054003-(4-Hydroxyphenyl) 5-methoxymethyl 2-oxazolidinoneHCID 132043233-Hydroxybutyl 4-methylbenzenesulfonate

Product 1

HCID 97961793-[4-(3-Hydroxybutoxy)phenyl]-5-methoxymethyl-2-oxazolidinoneYield 70%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 27.5 g (0.112 mol) of 1-tosyloxy-3-butanol in 250 ml of methylethylketone, are added 28.2 g (0.2 mol) of K2CO3 and 22.8 g (0.102 mol) of 3-(4-hydroxyphenyl)-5-methoxymethyl-2-oxazolidinone (code number MD 780232). The mixture is heated under reflux for 4 h 30. After filtration and concentration, the residue is taken up in 200 ml of CH2Cl2, the organic phase is washed with NaCl saturated water, dried over Na2SO4 and concentrated. After purification by flash chromatography (silica, eluent: CH2Cl2 : 98; CH3OH: 2), the aimed product is obtained with a 70% yield, m.p.: 58° C.;

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 4 h 30
  3. filtrationAfter filtration and concentration
  4. washthe organic phase is washed with NaCl saturated water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customAfter purification by flash chromatography (silica, eluent: CH2Cl2 : 98; CH3OH: 2)

Sources & evidence

ORD record
ord-6dccc781d1544c94a7d3423f73e24494
Source dataset
uspto-grants-1992_12
Patent number
US05171747

Reaction notes

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