Sodium Hydroxide → HCID 18916374, compound

HRID 1290617Notes

Reaction equation

HRID 1290617 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([F:24])([CH3:23])[CH:7]([O:12][C:13]1[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=1)[C:8]([O:10]C)=[O:9].[OH-].[Na+]>CO.O1CCCC1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([F:24])([CH3:23])[CH:7]([O:12][C:13]1[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[C:15]([O:21][CH3:22])[N:14]=1)[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15766823HCID 15766823, compound

Product 1

HCID 18916374HCID 18916374, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

0.9 g (3 mmol) of methyl 3-(2-thienyl)-3-fluoro-2-(4,6-dimethoxypyrimidin-2-yl)oxybutyrate (from Ex. 3) are dissolved in 20 ml of methanol and 20 ml of tetrahydrofuran, and 3.7 g of 10% strength NaOH solution are added. The mixture is stirred for 6 hours at 60° C. and for 12 hours at room temperature, the solvents are distilled off in vacuo, and the residue is taken up in 100 ml of water. The aqueous phase is now extracted using ethyl acetate and subsequently brought to pH 1-2 using dilute hydrochloric acid and extracted using ethyl acetate. After the mixture has been dried over magnesium sulfate and the solvent distilled off, a small amount of acetone is added to the residue and the precipitate which has formed is filtered off with suction. After drying, 0.8 g of a white powder remains.

Workup

  1. distillationthe solvents are distilled off in vacuo
  2. extractionThe aqueous phase is now extracted
  3. extractionextracted
  4. dry with materialAfter the mixture has been dried over magnesium sulfate
  5. distillationthe solvent distilled off
  6. additiona small amount of acetone is added to the residue
  7. customthe precipitate which has formed
  8. filtrationis filtered off with suction
  9. customAfter drying

Sources & evidence

ORD record
ord-91c675302d364e15a2fe535a64a2c04b
Source dataset
uspto-grants-1998_05
Patent number
US05753594

Reaction notes

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