(4-Methoxyphenyl)boronic acid → HCID 54169979, compound

HRID 1377905Notes

Reaction equation

HRID 1377905 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1)[CH3:2].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C([O-])(O)=O.[Na+]>COCCOC.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)=[CH:11][CH:10]=1)[CH3:2]

Participants

7

Reactant 3

HCID 201262(4-Methoxyphenyl)boronic acidHCID 516892Sodium BicarbonateHCID 53642638HCID 53642638, compound

Product 1

HCID 54169979HCID 54169979, compoundYield 57.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution in ethylene glycol dimethyl ether (30 mL) of 4-(4-iodophenoxy)butyric acid ethyl ester (0.50 g, 1.5 mmol), prepared as in Example 5, step 1, was added tetrakis(triphenylphosphine)palladium(0) (87 mg, 75 μM), and the mixture was stirred for 15 minutes. A solution in ethanol (9.6 mL) of 4-methoxyphenylboronic acid (0.25 g, 1.64 mmol) was then added. Saturated aqueous NaHCO3 (15 mL) was then poured in quickly and the reaction mixture was warmed to reflux and heated for one hour. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was partitioned between ethyl acetate and 10% aqueous Na2CO3. The organic phase was washed with 10% aqueous Na2CO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography on silica gel (20:1, then 10:1, then 5:1 hexane/ethyl acetate) gave 4-[4-(4-methoxyphenyl)phenoxy]butanoic acid ethyl ester (0.27 g, 57%) as white feathery needles.

Workup

  1. temperaturewas warmed
  2. temperatureto reflux
  3. temperatureheated for one hour
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between ethyl acetate and 10% aqueous Na2CO3
  6. washThe organic phase was washed with 10% aqueous Na2CO3 and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-600e11847d6d45799734fe452ae3a198
Source dataset
uspto-grants-1997_09
Patent number
US05665777

Reaction notes

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