Sodium Hydroxide → HCID 66718228, compound

HRID 1514742Notes

Reaction equation

HRID 1514742 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[C:13]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:14][O:15][C:16]=2[CH2:17][OH:18])=[N:6][CH:5]=1.[OH-].[Na+]>O1CCOCC1>[CH2:19]([C:13]1[C:12]([CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:23])=[O:2])=[CH:5][N:6]=2)=[C:16]([CH2:17][OH:18])[O:15][N:14]=1)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66718163HCID 66718163, compound

Product 1

HCID 66718228HCID 66718228, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 6-[3-butyl-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (490 mg, 1.53 mmol) in dioxane (20 mL) was added aqueous sodium hydroxide (2 M, 10 mL) and the reaction mixture was stirred at 90° C. for 17 h. The mixture was concentrated and the residue was acidified with aqueous hydrochloric acid (2 M, 15 mL) and extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated to a yellow oil to afford the title compound (480 mg, 100%). MS: m/e=305.4 [M−H]−.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to a yellow oil

Sources & evidence

ORD record
ord-3723b109b0dc43edac7941cd237f2374
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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