Water → HCID 23857599, compound

HRID 1708501Notes

Reaction equation

HRID 1708501 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]([O:12][CH3:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[CH:4]([O:12][CH3:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 12714665HCID 12714665, compound

Product 1

HCID 23857599HCID 23857599, compoundYield 17.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-methoxy-2-(4-hydroxyphenyl)acetic acid methyl ester (see Example 10) (8g; 40 mmol), potassium carbonate (11.04 g; 80 mmol) and 2-chloromethylpyridine hydrochloride (6.56 g; 40 mmol) in DMF (150 ml) was stirred at room temperature for 16 h, and then poured into icy water. The product was extracted with ethyl acetate, the acetate layer was washed with water, brine, dried with magnesium sulfate ans concentated in vacuo. The residue was purified by column chromatography (hexane-ethyl acetate 3:1) to afford 2.0 g of 2-methoxy-2-[4-(2-pyridylmethoxy)phenyl]acetic acid methyl ester.

Workup

  1. extractionThe product was extracted with ethyl acetate
  2. washthe acetate layer was washed with water, brine
  3. dry with materialdried with magnesium sulfate ans
  4. customThe residue was purified by column chromatography (hexane-ethyl acetate 3:1)

Sources & evidence

ORD record
ord-4987b06b8b52426a8e96ad876b9f595e
Source dataset
uspto-grants-1994_10
Patent number
US05358955

Reaction notes

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