Methanol → HCID 67983659, compound

HRID 1748184Notes

Reaction equation

HRID 1748184 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH3:15])[C:5]=2/[C:16](/Cl)=N/O)[CH2:3][CH2:2]1.[CH3:20][O-:21].[Na+].C[OH:24]>C(OCC)(=O)C.O>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH3:15])[C:5]=2[C:16]([O:21][CH3:20])=[O:24])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 88541843HCID 88541843, compound

Product 1

HCID 67983659HCID 67983659, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-cyclopropropyl-3-oxopropanoate (5.23 g, 36.8 mmol) and (Z)-5-cyclopropyl-N-hydroxy-3-(o-tolyl)isoxazole-4-carbimidoyl chloride (6.23 g, 36.8 mmol) were combined in anhydrous methanol (50 mL) and cooled to 0° C. under a nitrogen atmosphere. Sodium methoxide (25% in methanol, 11.0 mL, 44.2 mmol, 1.2 eq) was added dropwise and the mixture was allowed to warm to RT over 1 hour. The mixture was diluted with ethyl acetate (120 mL) and water (100 mL). The organic layer was separated and washed with brine (75 mL) then dried over magnesium sulfate and concentrated under vacuum. The oil was purified by column chromatography (SiO2, linear gradient, 0-100% ethyl acetate in hexanes) to afford the desired product. MS m/z 258.0 (M+1).

Workup

  1. temperatureto warm to RT over 1 hour
  2. customThe organic layer was separated
  3. washwashed with brine (75 mL)
  4. dry with materialthen dried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe oil was purified by column chromatography (SiO2, linear gradient, 0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-32b3469d78f84860af274af2e04f5137
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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