Potassium cyanate → 5-[2-(4-Hydroxy-3-methoxyphenyl)ethyl]-2,4-oxazolidinedione

HRID 1584362Notes

Reaction equation

HRID 1584362 reaction equation
[OH:1][CH:2]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([O:17][CH3:18])[CH:11]=1)[C:3]([O:5]CC)=O.[O-:19][C:20]#[N:21].[K+]>C(O)CCC>[OH:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][CH:2]2[O:1][C:20](=[O:19])[NH:21][C:3]2=[O:5])=[CH:11][C:12]=1[O:17][CH3:18]

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 21224421Ethyl 2-hydroxy-4-(4-hydroxy-3-methoxyphenyl)butanoate

Product 1

HCID 698306775-[2-(4-Hydroxy-3-methoxyphenyl)ethyl]-2,4-oxazolidinedioneYield 28%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of ethyl 2-hydroxy-4-(4-hydroxy-3-methoxyphenyl)butanoate (0.73 g), potassium cyanate (KCNO) (0.7 g) and butanol (25 ml) was stirred for 18 hours under reflux. The reaction mixture was concentrated under reduced pressure. The residue was poured into water and acidified with 2N HCl, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgSO4), followed by distilling off the solvent. The resulting oily product was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-chloroform (1:4, v/v), was obtained 5-[2-(4-hydroxy-3-methoxyphenyl)ethyl]-2,4-oxazolidinedione (0.2 g, 28%),

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was poured into water
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationby distilling off the solvent
  8. washFrom the fraction eluted with ethyl acetate-chloroform (1:4, v/v)

Sources & evidence

ORD record
ord-66b2a244eaeb4086b3532d083b2a3dd0
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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