Water → HCID 67388112, compound

HRID 910702Notes

Reaction equation

HRID 910702 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:9]=[C:10]([CH:13]=[O:14])[S:11][CH:12]=2)[CH:3]=1.[CH3:15][Mg]Br.O>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:9]=[C:10]([CH:13]([OH:14])[CH3:15])[S:11][CH:12]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 86628638HCID 86628638, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67388112HCID 67388112, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chloro-pyridin-2-yl)-thiophene-2-carbaldehyde (160 mg, 0.72 mmol) in THF (3 mL) was added methylmagnesium bromide (3 M, 1 mL) at −78° C. and the resulting mixture was stirred at the temperature for 3 hours. Water was added and THF was removed. The water solution was extracted with EtOAc and organic layer was concentrated. The resulting residue was purified by silica gel column to yield 1-[4-(4-chloro-pyridin-2-yl)-thiophen-2-yl]-ethanol

Workup

  1. customTHF was removed
  2. extractionThe water solution was extracted with EtOAc and organic layer
  3. concentrationwas concentrated
  4. customThe resulting residue was purified by silica gel column

Sources & evidence

ORD record
ord-ceb60c851f204e578d41fa9f1d63b569
Source dataset
uspto-grants-2011_09
Patent number
US08022209B2

Reaction notes

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