6-Phenylnicotinaldehyde → 1-(6-Phenylpyridin-3-yl)ethanol

HRID 1054083Notes

Reaction equation

HRID 1054083 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.[CH3:15][Mg]Br>>[C:1]1([C:7]2[N:8]=[CH:9][C:10]([CH:11]([OH:12])[CH3:15])=[CH:13][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 27645626-PhenylnicotinaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 675098951-(6-Phenylpyridin-3-yl)ethanol

Procedure

Synthesized using compound 43b (210 mg, 1.15 mmol) and methylmagnesium bromide (2.29 mL, 2.29 mmol, 1 M in THF) according to Method D. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (2:1) as eluent. Light yellow solid. Yield: 201 mg, 88%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=1.51 (d, J=6.6 Hz, 3H), 3.05 (br, s, 1H), 4.92 (q, J=6.6 Hz, 1H), 7.38-7.50 (m, 3H), 7.65 (d, J=7.9 Hz, 1H), 7.74 (dd, J=8.2, 2.2 Hz, 1H), 7.91-7.97 (m, 2H), 8.58 (d, J=2.2 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=25.0, 67.8, 120.4, 126.9, 128.7, 128.9, 134.0, 139.0, 139.5, 147.2, 156.6; MS (ESI): m/z=200.32 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-fe1fb903405349c4b34e1a2b327ac78a
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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