Potassium Hydroxide → HCID 54116628, compound

HRID 466480Notes

Reaction equation

HRID 466480 reaction equation
[C:1]([C:3](=[C:25]1[CH2:29][CH2:28][CH2:27][O:26]1)[C:4]1[C:5]([CH2:21][CH:22]([CH3:24])[CH3:23])=[C:6]([C:17]([O:19]C)=[O:18])[C:7]([CH:14]([F:16])[F:15])=[N:8][C:9]=1[C:10]([F:13])([F:12])[F:11])#[N:2].[OH-].[K+]>CO>[C:1]([C:3](=[C:25]1[CH2:29][CH2:28][CH2:27][O:26]1)[C:4]1[C:5]([CH2:21][CH:22]([CH3:24])[CH3:23])=[C:6]([C:17]([OH:19])=[O:18])[C:7]([CH:14]([F:16])[F:15])=[N:8][C:9]=1[C:10]([F:12])([F:11])[F:13])#[N:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86746206HCID 86746206, compound

Product 1

HCID 54116628HCID 54116628, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 10.0 g (23.9 mmol) of the compound of Example 2 in 100 mL methanol were added 14.7 g (223 mmol) KOH pellets (85%). The mixture was stirred at room temperature for 3 days and was then partitioned between ether and water. The aqueous layer was acidified with conc. HCl and extracted with ether. The ether layer was washed with brine, dried over magnesium sulfate, and filtered. The filtered. The filtrate was evaporated in vacuo and the residue was recrystallized from ethyl acetate/hexane to yield 8.9 g of the desired product as white crystals, a 93% yield. m.p. 192°-193° C.

Workup

  1. customwas then partitioned between ether and water
  2. extractionextracted with ether
  3. washThe ether layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo
  7. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-f518cbc09a5a4467948db5cc76695d19
Source dataset
uspto-grants-1992_10
Patent number
US05156670

Reaction notes

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