Potassium Carbonate → 5-(2R)-2-Oxiranyl-8-(phenylmethoxy)-2(1H)-quinolinone

HRID 1290067Notes

Reaction equation

HRID 1290067 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]([OH:23])[CH2:21]Cl)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:20]2[CH2:21][O:23]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 118096612(1H)-Quinolinone, 5-[(1R)-2-chloro-1-hydroxyethyl]-8-(phenylmethoxy)-

Product 1

HCID 114378125-(2R)-2-Oxiranyl-8-(phenylmethoxy)-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of (R)-8-benzyloxy-5-(2-chloro-1-hydroxyethyl)carbostyril (130 mg, 0.4 mMol) in acetone (10 ml) containing potassium carbonate (276 mg, 2 mMol) was stirred at 60° C. under an argon atmosphere for 18 hours. After cooling, the suspension was filtered and the filter pad was washed with acetone. The filtrates were combined and evaporated. Purification of the residue by chromatography on silica gel eluting with ethyl acetate gave the title compound as a pale yellow solid; m.p. 146°-150° C.; [α]D25 -30° (c=0.91, chloroform).

Workup

  1. temperatureAfter cooling
  2. filtrationthe suspension was filtered
  3. washthe filter pad was washed with acetone
  4. customevaporated
  5. customPurification of the residue by chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-9327334cfcf54dd5b492bc7a9cdc083a
Source dataset
uspto-grants-1998_05
Patent number
US05750701

Reaction notes

Loading…