3-Methoxy-4-pyridin-2-ylbenzaldehyde → HCID 21956527, compound

HRID 2213107Notes

Reaction equation

HRID 2213107 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)[CH:6]=[O:7].[CH2:17]([Mg]Br)[CH3:18]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]([OH:7])[CH2:17][CH3:18])[CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 219565123-Methoxy-4-pyridin-2-ylbenzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 21956527HCID 21956527, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-methoxy-4-pyridin-2-ylbenzaldehyde (150 mg, 0.7 mmol) in THF (3 mL) was cooled to 0° C. and was treated with ethyl magnesium bromide (0.9 mL of a 1M solution in THF, 0.9 mmol). The reaction mixture was kept at 0° C. for 2 h before quenching with water (5 mL). The product was extracted into CH2Cl2 (3×10 mL), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:4 to 1:1) to afford 1-(3-methoxy-4-pyridin-2-ylphenyl)propan-1-ol.

Workup

  1. custombefore quenching with water (5 mL)
  2. extractionThe product was extracted into CH2Cl2 (3×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on silica gel eluting with EtOAc:hexanes (1:4 to 1:1)

Sources & evidence

ORD record
ord-64923fe7f0d24f00aa0b8402cd64ecd2
Source dataset
uspto-grants-2006_09
Patent number
US07105533B2

Reaction notes

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