Potassium Hydroxide → HCID 15837481, compound

HRID 1871280Notes

Reaction equation

[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([O:12][CH:13]([C:18]([O:31][CH3:32])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]([O:16]C)=[O:15])[CH:3]=1.[OH-].[K+]>O1CCOCC1.O>[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([O:12][CH:13]([C:18]([O:31][CH3:32])([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:14]([OH:16])=[O:15])[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1.8 g (4.2 mmol) of methyl 2-(4-methyl-2-quinolinyloxy)-3-meth-oxy-3,3-diphenylpropionate were dissolved in 25 ml of dioxane, 8.4 ml of 1N KOH solution were added, and the mixture was stirred at 60° C. for 20 hours. The solution was diluted with 300 ml of water and extracted with ethyl acetate to remove unreacted ester and impurities. The aqueous phase was then adjusted to pH 1-2 with dilute hydrochloric acid and was extracted with ethyl acetate. Drying over magnesium sulfate and removal of the solvent by distillation resulted in 1.0 g of a foam. This was dissolved in a little ethyl acetate and left to stand at room temperature overnight, during which 265 mg of the product separated out as white crystals. Repetition of this procedure with the mother liquor afforded a further 166 mg of the product.

Workup

extractionextracted with ethyl acetate
customto remove unreacted ester and impurities
extractionwas extracted with ethyl acetate
dry with materialDrying over magnesium sulfate and removal of the solvent by distillation

Sources & evidence

ORD record: ord-b485e0b7a36a4b10a5bb311db40c9221
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06103732

Reaction notes

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