Potassium cyanate → HCID 69831630, compound

HRID 1584319Notes

Reaction equation

HRID 1584319 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([OH:25])[C:20]([O:22]CC)=O)=[CH:11][C:10]=1[O:26][CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:28][C:29]#[N:30].[K+]>C(O)CCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH:19]2[O:25][C:29](=[O:28])[NH:30][C:20]2=[O:22])=[CH:11][C:10]=1[O:26][CH3:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11378442Potassium cyanateHCID 21224443HCID 21224443, compound

Product 1

HCID 69831630HCID 69831630, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of ethyl 6-(4-benzyloxy-3-methoxyphenyl)-2-hydroxyhexanoate (15.22 g), potassium cyanate (KCNO) (13.26 g) and butanol (180 ml) was stirred for 72 hours under reflux. The reaction mixture was concentrated under reduced pressure. The residue was poured into water, which was acidified with 2N HCl, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), followed by distilling off the solvent. The residual oily product was subjected to column chromatography on silica gel. From the fraction eluted with ethyl acetate-hexane (1:1, v/v), was obtained 5-[4-(4-benzyloxy-3-methoxyphenyl)butyl]-2,4-oxazolidinedione (11.22 g, 74%), which was recrystallized from ethyl acetate-hexane to give colorless prisms, m.p.92-93° C.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionThe residue was poured into water, which
  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-hexane (1:1

Sources & evidence

ORD record
ord-392be92a692349558a03648d87cf004e
Source dataset
uspto-grants-1999_08
Patent number
US05932601

Reaction notes

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