Water → 2-(2-Chloro-5-methoxy-phenyl)-1-(2-chloro-pyridin-4-yl)-propan-1-ol

HRID 333807Notes

Reaction equation

HRID 333807 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N:3]=1.C([Mg]Cl)(C)C.[Cl-].[Li+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[CH:25]([CH3:28])[CH:26]=[O:27].O>C1COCC1>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[CH:25]([CH3:28])[CH:26]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1)[OH:27]

Participants

6

Reactant 4

HCID 962WaterHCID 15165112-Chloro-4-iodopyridineHCID 574499712-(2-Chloro-5-methoxy-phenyl)-propionaldehydeHCID 178461733HCID 178461733, compound

Product 1

HCID 866291052-(2-Chloro-5-methoxy-phenyl)-1-(2-chloro-pyridin-4-yl)-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Chloro-4-iodopyridine (1.03 g, CAS Reg. No. 153034-86-7) was dissolved in THF (50 mL) and a solution of isopropylmagnesiumchloride-lithium chloride complex (14% in THF, 3.13 mL) was added at RT over 3 minutes. The mixture was cooled in an ice bath and 2-(2-chloro-5-methoxy-phenyl)-propionaldehyde (710 mg) dissolved in THF (20 mL) was added drop wise over a period of 10 minutes. Stirring was continued for 1.5 hours. The reaction mixture was poured into water, extracted with ethyl acetate and the organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane) to give the desired compound as a yellow oil (734 mg). MS (m/e)=312.0 (MH+).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. additionwas added drop wise over a period of 10 minutes
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane)

Sources & evidence

ORD record
ord-48adf247808c4790bc19197b4241b34e
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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