Water → HCID 42629767, compound

HRID 548808Notes

Reaction equation

HRID 548808 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14].[H-].[Na+].Cl[C:18]1[N:19]=[N:20][C:21]([CH3:24])=[CH:22][CH:23]=1.O>C1COCC1>[CH3:24][C:21]1[N:20]=[N:19][C:18]([O:14][CH2:13][C:3]2[C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2272543-Chloro-6-methylpyridazineHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanol

Product 1

HCID 42629767HCID 42629767, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-methyl-3-phenyl-4-isoxazolyl)methanol (0.50 g, 2.64 mmol) in THF (8 mL) was added sodium hydride (55% dispersion in mineral oil, 0.16 g, 3.17 mmol) at 0° C. The reaction mixture was stirred for 30 min while it was allowed to warm up to room temperature. 3-Chloro-6-methylpyridazine (0.36 g, 2.77 mmol) was added and stirring was continued for 2 h. Water (10 mL) was added and the mixture was extracted with ethyl acetate (40 mL). The combined organic layers were washed with brine (10 mL) and dried over sodium sulfate. Concentration and purification of the residue by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50) afforded the title compound (220 mg, 30%) as a yellow oil. MS: m/e=282.3 [M+H]−.

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. extractionthe mixture was extracted with ethyl acetate (40 mL)
  4. washThe combined organic layers were washed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration and purification of the residue by chromatography (SiO2, heptane:ethyl acetate=100:0 to 50:50)

Sources & evidence

ORD record
ord-026e1138580344d8a0d899b29b74cddc
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

Loading…