Potassium Hydroxide → HCID 86635775, compound

HRID 1919319Notes

Reaction equation

HRID 1919319 reaction equation
[OH-].[K+:2].[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[N+:12]([CH2:14][C:15]([O:17]C)=[O:16])#[C-:13]>CO>[F:3][C:4]1[CH:11]=[CH:10][C:7]([C@@H:8]2[O:9][CH:13]=[N:12][C@H:14]2[C:15]([O-:17])=[O:16])=[CH:6][CH:5]=1.[K+:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 680234-FluorobenzaldehydeHCID 547815Methyl isocyanoacetate

Product 1

HCID 86635775HCID 86635775, compoundYield 106.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred and cooled (4° C.) solution of KOH (3.04 g, 46.02 mmol) in MeOH (50 mL) were slowly added 4-fluorobenzaldehyde (4.13 mL, 38.35 mmol) and methyl 2-isocyanoacetate (4.00 g, 38.35 mmol). This mixture was stirred at RT under N2 atmosphere for 7 h. The solvent was evaporated and the residue was dried overnight under vacuum to give potassium (±)-threo-5-(4-fluorophenyl)-4,5-dihydrooxazole-4-carboxylate ANP 20162 (10.09 g, quantitative yield), as a beige powder. This material was used in the next reaction without further purification.

Workup

  1. stirringThis mixture was stirred at RT under N2 atmosphere for 7 h
  2. customThe solvent was evaporated
  3. customthe residue was dried overnight under vacuum

Sources & evidence

ORD record
ord-4271897c1a504fb5b8d969f68f91ec62
Source dataset
uspto-grants-2012_05
Patent number
US08168631B2

Reaction notes

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