Sodium Hydroxide → HCID 131735495, compound

HRID 520324Notes

Reaction equation

HRID 520324 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:11]([C:17]([O:19]C)=[O:18])=[N:12][CH:13]=[CH:14][C:15]=1[Cl:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C.O>[Si:1]([O:8][CH2:9][C:10]1[C:11]([C:17]([OH:19])=[O:18])=[N:12][CH:13]=[CH:14][C:15]=1[Cl:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 131735496HCID 131735496, compound

Product 1

HCID 131735495HCID 131735495, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
19 °C

Procedure

A mixture of 160d (25 g, 76 mmol) and sodium hydroxide (6.1 g, 152 mmol) in ethanol (200 mL) and water (200 mL) was stirred at 19° C. for 2 h. See FIG. 5. The mixture was diluted with water (200 mL) and the resulting mixture was extracted with EtOAc (200 mL×2). The organic layers were washed with brine (80 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford 3-(((tert-butyldimethylsilyl)oxy)methyl)-4-chloropicolinic acid 160e (20 g, 87%) as a white solid.

Workup

  1. extractionthe resulting mixture was extracted with EtOAc (200 mL×2)
  2. washThe organic layers were washed with brine (80 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79e6c71ca21f4b23a3000e29008a6367
Source dataset
uspto-grants-2016_05
Patent number
US09326985B2

Reaction notes

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