Sodium Hydroxide → HCID 15056706, compound

HRID 1590008Notes

Reaction equation

HRID 1590008 reaction equation
[OH-].[Na+].[C:3]([C:6]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([C:15]([O:17]C)=[O:16])[O:8][N:7]=1)([CH3:5])=[CH2:4]>O.CO>[C:3]([C:6]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([C:15]([OH:17])=[O:16])[O:8][N:7]=1)([CH3:5])=[CH2:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15056705HCID 15056705, compound

Product 1

HCID 15056706HCID 15056706, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

At 0° C., a solution of 3.6 g (0.09 mol) of sodium hydroxide in 75 ml of water was dripped into 20.0 g (0.09 mol) of dimethyl 3-isopropenylisoxazole-4,5-dicarboxylate (from stage A.1) in 150 ml of methanol, and the mixture was stirred for 14 hours at room temperature. 250 ml of water was added, the pH was adjusted to 8, extraction was effected with 200 ml of dichloroethane, and the aqueous phase was adjusted to a pH of 1-2 with 6N hydrochloric acid and extracted three times, each time with 250 ml of dichloromethane. The combined organic extracts were dried over magnesium sulfate and the solvent was distilled off under reduced pressure. Yield: 97%; 1H-NMR (in CDCl3): δ=2.12 ppm (s; 3H), 4.07 ppm (s; 3H), 5.41 ppm (m; 2H); 8.00 ppm (bs; 1H).

Workup

  1. customAt 0° C.
  2. extractionthe pH was adjusted to 8, extraction
  3. extractionextracted three times
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4f867e829af04cb2954ec69e64fd8fd2
Source dataset
uspto-grants-1993_04
Patent number
US05201932

Reaction notes

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