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

HRID 257851Notes

Reaction equation

HRID 257851 reaction equation
C([O-])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:18][CH:17]([CH2:19][O:20][CH3:21])[O:16][C:15]2=[O:22])=[CH:10][CH:9]=1.S(O[CH2:34][CH2:35][CH:36]([OH:38])[CH3:37])(C1C=CC(C)=CC=1)(=O)=O>C(C(C)=O)C>[OH:38][CH:36]([CH3:37])[CH2:35][CH2:34][O:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:18][CH:17]([CH2:19][O:20][CH3:21])[O:16][C:15]2=[O:22])=[CH:12][CH:13]=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

28.2 g (0.2 mol) of K2CO3 and 22.8 g (0.102 mol) of 3-(4-hydroxyphenyl) 5-methoxymethyl 2-oxazolidinone (Code No. 780232) were added to a solution of 27.5 g (0.112 mol) of 1-tosyloxy 3-butanol in 250 ml of methyl ethyl ketone. The mixture was reflux-heated for 41/2 hours. After filtration and concentration, the residue was dissolved in 200 ml CH2Cl2 and the organic phase was washed with water saturated with NaCl, dried over Na2SO4 and concentrated. After purification by chromatographic flash [silica, eluent: CH2Cl2 (98)/CH3OH(2)], the expected product was obtained with a 70% yield:

Workup

  1. temperatureThe mixture was reflux-heated for 41/2 hours
  2. filtrationAfter filtration and concentration
  3. dissolutionthe residue was dissolved in 200 ml CH2Cl2
  4. washthe organic phase was washed with water saturated with NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customAfter purification by chromatographic flash [silica, eluent: CH2Cl2 (98)/CH3OH(2)]

Sources & evidence

ORD record
ord-d252c695079d4ae4a1cb59e44df37869
Source dataset
uspto-grants-1993_11
Patent number
US05264443

Reaction notes

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