beta-Chloroethyl acetate → Ethyl 2-(2-pyridinylmethoxy)acetate

HRID 1369901Notes

Reaction equation

HRID 1369901 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[C:11]([O:14][CH2:15][CH2:16]Cl)(=[O:13])[CH3:12].OP([O-])(O)=O.[Na+]>CN(C=O)C>[N:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][O:3][CH2:12][C:11]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 10959beta-Chloroethyl acetateHCID 11474PiconolHCID 24758Sodium hydrideHCID 23672064Monosodium phosphate

Product 1

HCID 18516696Ethyl 2-(2-pyridinylmethoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.530 g of sodium hydride is added over 20 minutes at 0° C. to a solution of 1 g of 2-hydroxymethylpyridine and DMF. 1.6 ml of chloroethyl acetate is added at 0° C. 2 ml of a solution of sodium acid phosphate is poured in, then the reaction medium is concentrated under reduced pressure. The product obtained is chromatographed on silica eluting with a methylene chloride methanol mixture 90-10. 4.5 g of product is obtained which is chromatographed on silica eluting with a methylene chloride, methanol mixture 90-10. The product is obtained is purified and 1.30 g of sought product is obtained.

Workup

  1. concentrationis concentrated under reduced pressure
  2. customThe product obtained
  3. customis chromatographed on silica eluting with a methylene chloride methanol mixture 90-10

Sources & evidence

ORD record
ord-8770c007e95548f0877bf6f29af58706
Source dataset
uspto-grants-2003_06
Patent number
US06579902B1

Reaction notes

Loading…