Sodium Hydroxide → HCID 15682539, compound

HRID 1590006Notes

Reaction equation

HRID 1590006 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[C:9]([C:14]([O:16]C)=[O:15])=[N:10][O:11][C:12]=1[CH3:13])=[O:7])[CH3:4]>O.O1CCCC1>[CH2:3]([O:5][C:6]([C:8]1[C:9]([C:14]([OH:16])=[O:15])=[N:10][O:11][C:12]=1[CH3:13])=[O:7])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15682534HCID 15682534, compound

Product 1

HCID 15682539HCID 15682539, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

At -15° to -10° C. and under a nitrogen blanket, 4.7 g (0.117 mol) of sodium hydroxide in 80 ml of water was dripped into 25.0 g (0.117 mol) of methyl 4-ethoxycarbonyl-5-methylisoxazole-3-carboxylate in 200 ml of anhydrous tetrahydrofuran, and the mixture was stirred for 12 hours. The solvents were stripped off in a rotary evaporator (bath temperature: 30°-35° C.), the residue was taken up in 250 ml of water, the pH was adjusted to 8-9 with hydrochloric acid, and the mixture was extracted twice, each time with 150 ml of diethylether. The aqueous phase was acidified to a pH of 2 with 6N HCl and extracted four times, each time with 250 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate and the solvent was stripped off under reduced pressure. Yield: 70%; 1H-NMR (250 MHz; CDCl3); δ=1.42 ppm (t; 3H), 2.80 ppm (s; 3H), 4.59 ppm (q; 2H).

Workup

  1. customAt -15° to -10° C.
  2. customThe solvents were stripped off in a rotary evaporator (bath temperature: 30°-35° C.)
  3. extractionthe mixture was extracted twice
  4. extractionextracted four times
  5. dry with materialThe combined organic phases were dried over magnesium sulfate

Sources & evidence

ORD record
ord-85d2409a47e046b28f3c3429ae396d43
Source dataset
uspto-grants-1993_04
Patent number
US05201932

Reaction notes

Loading…