6-Phenylnicotinaldehyde → Furan-2-yl(6-phenylpyridin-3-yl)methanol

HRID 1054101Notes

Reaction equation

HRID 1054101 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.[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[Mg]Br>>[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[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 178419635HCID 178419635, compound

Product 1

HCID 67511653Furan-2-yl(6-phenylpyridin-3-yl)methanol

Procedure

Synthesized using compound 43b (650 mg, 3.75 mmol) and furan-2-ylmagnesium bromide (1.85 g, 10.8 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 (6:1) as eluent. Yellow solid. Yield: 631 mg, 67%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=3.62 (br. s., 1H), 5.86 (s, 1H), 6.17 (d, J=3.4 Hz, 1H), 6.33 (dd, J=3.0, 1.8 Hz, 1H), 7.33-7.51 (m, 4H), 7.69 (d, J=7.9 Hz, 1H), 7.83 (dd, J=8.2, 1.8 Hz, 1H), 7.88-7.99 (m, 2H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=66.7, 106.7, 109.3, 119.4, 126.0, 127.7, 128.0, 134.0, 134.3, 137.9, 141.8, 147.1, 154.1, 156.1; (ESI): m/z=251.87 [M+H]+.

Workup

  1. customSynthesized
  2. customCrude product was purified by flash chromatography on silica-gel
  3. additiona mixture of hexane/ethyl acetate (6:1) as eluent

Sources & evidence

ORD record
ord-9bc5776e34734723b67fd800a3585900
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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