6-Phenylnicotinaldehyde → Phenyl(6-phenylpyridin-3-yl)methanol

HRID 1054099Notes

Reaction equation

HRID 1054099 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.[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:15]1([CH:11]([C:10]2[CH:9]=[N:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:14][CH:13]=2)[OH:12])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 27645626-PhenylnicotinaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 67509892Phenyl(6-phenylpyridin-3-yl)methanol

Procedure

Synthesized using compound 43b (300 mg, 1.73 mmol) and phenylmagnesium bromide (1.73 mL, 3.46 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 (3:1) as eluent. Yellow solid. Yield: 138 mg, 42%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=5.91 (s, 1H), 7.29-7.34 (m, 1H), 7.35-7.50 (m, 7H), 7.68 (dd, J=8.2, 0.6 Hz, 1H), 7.73-7.78 (m, 1H), 7.94-7.99 (m, 2H), 8.68 (dd, J=1.6, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=74.1, 120.3, 126.5, 126.9, 128.0, 128.7, 128.7, 128.9, 135.0, 137.6, 139.0, 143.0, 148.2, 156.7; (ESI): m/z=261.97 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-50c4ca34cfdf453f8e690b7edf479de9
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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