Sodium Hydroxide → HCID 22270329, compound

HRID 1160727Notes

Reaction equation

HRID 1160727 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][N:11]=1)([CH3:8])[C:3]([O:5]CC)=[O:4].[OH-].[Na+]>CO.C1COCC1.O>[CH3:8][C:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][N:11]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 22270701HCID 22270701, compound

Product 1

HCID 22270329HCID 22270329, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-methyl-2-(5-methylsulfonyl-2-pyridyloxy)propionate (Step A, 0.45 g, 1.6 mol) in 5 mL MeOH, 10 mL THF and 10 mL water was added sodium hydroxide (0.19 g, 4.7 mmol). After stirring at room temperature for 3 days, the reaction mixture was partially concentrated, and was added 2 M hydrochloric acid to pH>2. The resulting mixture was extracted with EtOAc (2×20 mL), and the combined extracts were dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to afford the title compound. 1H NMR (500 MHz, CD3OD): δ 8.60 (d, 1H), 8.16 (dd, 1H), 7.17 (d, 1H), 3.15 (s, 3H), 1.71 (s, 6H).

Workup

  1. concentrationthe reaction mixture was partially concentrated
  2. additionwas added 2 M hydrochloric acid to pH>2
  3. extractionThe resulting mixture was extracted with EtOAc (2×20 mL)
  4. dry with materialthe combined extracts were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2aefd6a39ae0434090b5f378d2aaacb9
Source dataset
uspto-grants-2010_10
Patent number
US07816534B2

Reaction notes

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