Water → HCID 66643579, compound

HRID 1807488Notes

Reaction equation

HRID 1807488 reaction equation
[H-].[Na+].[CH3:3][C:4]1[O:8][N:7]=[C:6]([CH2:9][CH2:10][CH3:11])[C:5]=1[CH2:12][OH:13].Cl[C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][N:16]=1.O>C1COCC1>[CH3:22][O:21][C:19](=[O:20])[C:18]1[CH:23]=[CH:24][C:15]([O:13][CH2:12][C:5]2[C:6]([CH2:9][CH2:10][CH3:11])=[N:7][O:8][C:4]=2[CH3:3])=[N:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 66643639HCID 66643639, compound

Product 1

HCID 66643579HCID 66643579, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred suspension of sodium hydride (2.78 g of a 60% dispersion in mineral oil, 64 mmol) in THF (40 mL) at 0° C. and under argon was added solution of (5-methyl-3-propyl-isoxazol-4-yl)-methanol (7.60 g, 49 mmol) in tetrahydrofuran (40 mL) dropwise. The mixture was warmed to ambient temperature, stirred for 30 min, then cooled to 0° C. and a solution of methyl 6-chloronicotinate (8.40 g, 49 mmol) in THF (40 mL) was added dropwise. The reaction mixture was warmed to room temperature. After 2 h, water was added then the resulting mixture extracted with ethyl acetate. The combined organic extracts were dried, filtered and concentrated. Purification by chromatography (silica, 0 to 20% ethyl acetate in heptane) gave the title compound (8.4 g, 50%) as a light yellow oil. MS: m/e=413.2 [M+H]+.

Workup

  1. temperaturecooled to 0° C.
  2. temperatureThe reaction mixture was warmed to room temperature
  3. waitAfter 2 h
  4. extractionthe resulting mixture extracted with ethyl acetate
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by chromatography (silica, 0 to 20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-1c84c36a28b0426aaf12ac4764bc7208
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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