Formic Acid → 2-(6-Methyl-3-pyridyloxy)-2-methylpropionic Acid

HRID 488629Notes

Reaction equation

HRID 488629 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[K+].C(O)=O>CS(C)=O.O>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]([CH3:16])([CH3:15])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 14797Potassium HydroxideHCID 222705742-Methyl-2-(6-methyl-pyridin-3-yloxy)-propionic acid ethyl ester

Product 1

HCID 222704032-(6-Methyl-3-pyridyloxy)-2-methylpropionic Acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a solution of ethyl 2-(6-methyl-3-pyridyloxy)-2-methylpropionate (Step A, 2.0 g, 8.9 mmol) in DMSO (20 mL) was added potasium hydroxide (1.0 g, 20 mmol) in 2 mL water. After stirring at room temperature for 2 h, the reaction was quenched by addition of formic acid (85%, 10 mmol) and poured into water (200 mL). The product was extracted with EtOAc (2×100 mL), and the combined extracts were dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give the title compound contaminated with DMSO (molar ratio 1:5, determined by NMR). 1H NMR (500 MHz, CD3OD): δ 8.06 (d, 1H), 7.38-7.22 (m, 2H), 2.47 (s, 3H), 1.58 (s, 6H).

Workup

  1. extractionThe product was extracted with EtOAc (2×100 mL)
  2. dry with materialthe combined extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-910c1c2e6f37448088bd06fdfdb76601
Source dataset
uspto-grants-2005_12
Patent number
US06972295B2

Reaction notes

Loading…