Ethyl chloroacetate → 2-[2-(2-Ethoxy-phenoxy)-1-(2-pyridinyl)ethoxy]acetic acid ethyl ester

HRID 1762914Notes

Reaction equation

HRID 1762914 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:21]=[CH:20][CH:19]=[CH:18][C:7]=1[O:8][CH2:9][CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[OH:11])[CH3:4].Cl[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>O1CCCC1>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][O:11][CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)[CH2:9][O:8][C:7]1[CH:18]=[CH:19][CH:20]=[CH:21][C:6]=1[O:5][CH2:3][CH3:4])[CH3:28]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 24758Sodium hydrideHCID 14500438alpha-[(2-Ethoxyphenoxy)methyl]-2-pyridinemethanol

Product 1

HCID 544050012-[2-(2-Ethoxy-phenoxy)-1-(2-pyridinyl)ethoxy]acetic acid ethyl esterYield 82.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A mixture of sodium hydride (50%, 9.79 g, 0.204 mole, washed with hexane) in tetrahydrofuran (THF) was prepared. α-[(2-Ethoxyphenoxy)methyl]-2-pyridinemethanol (52.96 g, 0.204 mole) in 175 ml of THF was added dropwise under nitrogen with stirring over 1/2 hr. Stirring was continued for 1 hr at room temperature. Ethyl chloroacetate (24.98 g, 0.204 mole) in THF was added dropwise over 10 min. The resulting solution was heated at reflux for 2 hr and stirred at room temperature (72 hr). THF was removed, and the residue partitioned between diethyl ether and water. Removal of diethyl ether gave 57.9 g (0.168 mole, 82.4% yield) of the desired 2-[2-(2-ethoxy-phenoxy)-1-(2-pyridinyl)ethoxy]acetic acid ethyl ester as an oil. This structure of the product was confirmed by NMR.

Workup

  1. customwas prepared
  2. stirringStirring
  3. waitwas continued for 1 hr at room temperature
  4. temperatureThe resulting solution was heated
  5. temperatureat reflux for 2 hr
  6. stirringstirred at room temperature (72 hr)
  7. customTHF was removed
  8. customthe residue partitioned between diethyl ether and water
  9. customRemoval of diethyl ether

Sources & evidence

ORD record
ord-9a1d0810e8c04ffb8f840b3a1de5fbfb
Source dataset
uspto-grants-1989_05
Patent number
US04835164

Reaction notes

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