Isobutylene oxide → HCID 22116058, compound

HRID 1885635Notes

Reaction equation

HRID 1885635 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH2:13][O:14][C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=3)[CH2:10][C:9]2=[O:25])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:32][C:33]1([O:36][CH2:35]1)[CH3:34]>CN(C)C=O>[OH:36][C:33]([CH3:35])([CH3:34])[CH2:32][O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH2:13][O:14][C:15]3[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=3)[CH2:10][C:9]2=[O:25])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11208Isobutylene oxide2×HCID 11430Potassium CarbonateHCID 10382682HCID 10382682, compound

Product 1

HCID 22116058HCID 22116058, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 4-[1-[4-hydroxyphenyl)-2-pyrrolidon-4-yl]methoxybenzoate (2.00 g) and potassium carbonate (1.62 g) are dissolved and suspended in dimethylformamide (20 ml) and thereto is added isobutylene oxide (1.06 ml). The mixture is stirred at 80° C. for 17 hours and thereto is added isobutylene oxide (1.06 ml), and the mixture is further heated with stirring for 5 hours. The reaction mixture is concentrated under reduced pressure and thereto is added water. The insoluble material is collected by filtration, washed with water and recrystallized from about 30% aqueous methanol to give the desired product (2.15 g), m.p. 89.5°-90.5° C.

Workup

  1. temperaturethe mixture is further heated
  2. stirringwith stirring for 5 hours
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. additionis added water
  5. filtrationThe insoluble material is collected by filtration
  6. washwashed with water
  7. customrecrystallized from about 30% aqueous methanol

Sources & evidence

ORD record
ord-aef48331866043febfe679cda74bd4ba
Source dataset
uspto-grants-1992_09
Patent number
US05145865

Reaction notes

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