Diethyl Ether → 2-(6-Chloropyridin-3-yl)propan-2-ol

HRID 449549Notes

Reaction equation

HRID 449549 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5](C(Cl)=O)=[CH:4][N:3]=1.[CH3:11][Mg]I.C([O:16][CH2:17][CH3:18])C>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:17]([OH:16])([CH3:18])[CH3:11])=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 27821656-Chloronicotinoyl ChlorideHCID 178418373HCID 178418373, compound

Product 1

HCID 125621182-(6-Chloropyridin-3-yl)propan-2-ol

Procedure

A solution of 6-chloronicotinoyl chloride (38.037 g, 216 mmol, Eq: 1.00) in anhydrous diethyl ether (200 ml) was added dropwise to a stirred 3 M methylmagnesium iodide solution (158 ml, 475 mmol, Eq: 2.2) at room temperature. After the addition the reaction mixture was refluxed for 3 hours. Reaction was quenched by pouring it to a stirred mixture of ice/200 ml acetic acid; sodium bicarbonate was added until pH 8; extracted with diethyl ether; washed with brine; dried over sodium sulfate; filtered; concentrated to give a yellow solid (30.15 g, 0.175 mol)

Workup

  1. additionAfter the addition the reaction mixture
  2. temperaturewas refluxed for 3 hours
  3. customReaction
  4. customwas quenched
  5. additionby pouring it
  6. additionto a stirred mixture of ice/200 ml acetic acid
  7. additionsodium bicarbonate was added until pH 8
  8. extractionextracted with diethyl ether
  9. washwashed with brine
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-8f114bbd413648a1aed13926d70b7952
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

Loading…