Potassium Hydroxide → HCID 86717842, compound

HRID 591045Notes

Reaction equation

HRID 591045 reaction equation
[C:1]([O:5][CH:6]([C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]2[C:19]=1[C:20]1[CH:21]=[CH:22][C:23]2[O:28][CH2:27][CH2:26][CH2:25][C:24]=2[CH:29]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>C(O)C.O>[C:1]([O:5][CH:6]([C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]2[C:19]=1[C:20]1[CH:21]=[CH:22][C:23]2[O:28][CH2:27][CH2:26][CH2:25][C:24]=2[CH:29]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86717841HCID 86717841, compound

Product 1

HCID 86717842HCID 86717842, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 2-(tert-butoxy)-2-[3-(3,4-dihydro-2H-1-benzopyran-6-yl)imidazo[1,2-a]pyridin-2-yl]acetate (25e) (31 mg, 0.079 mmol) and potassium hydroxide (18 mg, 0.37 mmol) in a mixture of ethanol (3 mL) and water (1 mL) was refluxed for 1 hour. The mixture was concentrated in vacuo. Water (1 mL) was added to the residue and the aqueous layer was extracted with ethyl acetate (5 mL). The aqueous layer was acidified with 1M hydrochloric acid until pH 7 and extracted with dichloromethane (2×5 mL). The organic layer was concentrated in vacuo to provide the desired acid (17 mg, 0.044 mmol, 56%) as a beige solid.

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationThe mixture was concentrated in vacuo
  3. additionWater (1 mL) was added to the residue
  4. extractionthe aqueous layer was extracted with ethyl acetate (5 mL)
  5. extractionextracted with dichloromethane (2×5 mL)
  6. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-394242403bd5481cac830480e7f7244d
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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