6-Phenylnicotinaldehyde → 2-Methyl-1-(6-phenylpyridin-3-yl)propan-1-ol

HRID 1054079Notes

Reaction equation

HRID 1054079 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=[O:12])=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15]([Mg]Cl)([CH3:17])[CH3:16]>>[CH3:16][CH:15]([CH3:17])[CH:11]([C:10]1[CH:9]=[N:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:14][CH:13]=1)[OH:12]

Participants

3

Reactant 2

HCID 27645626-PhenylnicotinaldehydeHCID 178418918HCID 178418918, compound

Product 1

HCID 675104242-Methyl-1-(6-phenylpyridin-3-yl)propan-1-ol

Procedure

Synthesized using compound 43b (283 mg, 1.55 mmol) and isopropylmagnesium chloride (1.55 mL, 3.10 mmol, 2 M in THF) according to Method D. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (4:1) as eluent. Orange solid. Yield: 138 mg, 40%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=0.82-0.93 (m, 3H), 1.02 (d, J=6.6 Hz, 3H), 1.95-2.08 (m, 1H), 4.46 (d, J=6.6 Hz, 1H), 7.39-7.44 (m, 1H), 7.45-7.50 (m, 2H), 7.68-7.75 (m, 2H), 7.96-8.01 (m, 2H), 8.57 (d, J=1.9 Hz, H); MS (ESI): m/z=228.26 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (4:1) as eluent

Sources & evidence

ORD record
ord-95e95a67e28444a9a339201367d0a213
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

Loading…