Hydrochloric Acid → HCID 66618938, compound

HRID 1942285Notes

Reaction equation

HRID 1942285 reaction equation
C([Li])CCC.[CH3:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=1.Cl[CH2:17][C:18]1[C:19]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:20][O:21][C:22]=1[CH3:23].Cl>C1COCC1>[CH3:23][C:22]1[O:21][N:20]=[C:19]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:18]=1[CH2:17][CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1378606-Methylnicotinic acidHCID 11052826Isoxazole, 4-(chloromethyl)-5-methyl-3-phenyl-HCID 178418339Butyllithium

Product 1

HCID 66618938HCID 66618938, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-74 °C

Procedure

n-Butyllithium solution was added dropwise to a stirred suspension of 6-methylnicotinic acid (137 mg, 1.0 mmol) in THF (3 mL) over 30 min at −74° C. After 1 h a solution of 4-chloromethyl-5-methyl-3-phenyl-isoxazole (208 mg, 1.0 mmol) in THF (3 mL) was added dropwise such that the temperature did not exceed −68° C. The reaction mixture was stirred at −74° C. for 1 h, then HCl (1 N, 10 mL) added and the reaction mixture warmed to room temperature and extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated. Purification by chromatography (silica, heptane:ethyl acetate=100:0 to 9:1) afforded the title compound (20 mg, 6%) as a light yellow oil. MS: m/e=168.3 [M+H]+.

Workup

  1. customdid not exceed −68° C
  2. temperaturethe reaction mixture warmed to room temperature
  3. extractionextracted with ethyl acetate
  4. customThe combined organic extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by chromatography (silica, heptane:ethyl acetate=100:0 to 9:1)

Sources & evidence

ORD record
ord-d1c994ff19d449b2a6523d55b341f990
Source dataset
uspto-grants-2013_03
Patent number
US08389550B2

Reaction notes

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