Water → 2-(6-Chloro-2-methoxypyridin-3-yl)ethan-1-ol

HRID 861624Notes

Reaction equation

HRID 861624 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.[Li]CCCC.[CH2:15]1[O:17][CH2:16]1.O>C1COCC1.CCOCC>[OH:17][CH2:16][CH2:15][C:5]1[C:4]([O:8][CH3:9])=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6354Ethylene OxideHCID 870092-Chloro-6-methoxypyridineHCID 178418339Butyllithium

Product 1

HCID 197036802-(6-Chloro-2-methoxypyridin-3-yl)ethan-1-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.0 g (7.0 mmol) of 2-chloro-6-methoxypyridine in 20 ml of dry THF cooled to -78° C. was added 10.9 ml (1.6M in hexanes, 17.4 mmol) n-BuLi under an atmosphere of nitrogen. The temperature of the mixture was allowed to raise to -40° C. before an addition of 4 ml ethylene oxide in 6 ml ether. The mixture was warmed to room temperature, 50 ml water was added and the aqueous layer was separated and extracted with 2×100 ml EtOAc. The organic extracts were combined, washed once with water, dried with Na2SO4, and concentrated in vacuo. The crude material was purified by dry column flash chromatography (hexane/EtOAc) to afford 0.22 g of 3-(2-hydroxyethyl)-6-chloro-2-methoxypyridine as a yellowish oil.

Workup

  1. customthe aqueous layer was separated
  2. extractionextracted with 2×100 ml EtOAc
  3. washwashed once with water
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified
  7. dry with materialby dry column flash chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-201f2eacdbc24711aac5aed533139453
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

Loading…