Ethanol → HCID 71814872, compound

HRID 2279280Notes

Reaction equation

HRID 2279280 reaction equation
C([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][N:8]1[C:12](=[O:13])/[C:11](=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[B:22]([F:24])[F:23])/[N:10]=[C:9]1[CH3:25])C.C(O)C.[OH-].[Na+]>O>[F:24][B:22]([F:23])[C:16]1[CH:17]=[C:18]([OH:21])[CH:19]=[CH:20][C:15]=1/[CH:14]=[C:11]1\[N:10]=[C:9]([CH3:25])[N:8]([CH2:7][CH2:6][CH2:5][C:4]([OH:26])=[O:3])[C:12]\1=[O:13]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 71814871HCID 71814871, compound

Product 1

HCID 71814872HCID 71814872, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(Z)-ethyl-4-(4-(2-(difluoroboryl)-4-hydroxybenzylidene)-2-methyl-5-oxo-4,5-dihydro-1H-imidazole-1-yl)butyrate (1.82 g, 5.0 mmol) was dissolved in water (200 mL), then ethanol (50 mL) and sodium hydroxide (400 mg, 10.0 mmol) were added. The mixture was stirred for 2 hours at r.t., then acidified with aqueous HF solution and extracted with ethyl acetate (3×100 mL), washed with water (1×50 mL) and dried over anhydrous sodium sulfate. The mixture was evaporated and purified by column chromatography (chloroform:ethanol—5:1): 1.29 g. (Yield 77%)

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washwashed with water (1×50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe mixture was evaporated
  5. custompurified by column chromatography (chloroform:ethanol—5:1)

Sources & evidence

ORD record
ord-0738c38a156145a59c90c70ae78b9b2b
Source dataset
uspto-grants-2015_09
Patent number
US09133220B2

Reaction notes

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