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

HRID 1054085Notes

Reaction equation

HRID 1054085 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]1([Mg]Br)[CH2:17][CH2:16]1>>[CH: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])[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 27645626-PhenylnicotinaldehydeHCID 178418630HCID 178418630, compound

Product 1

HCID 67510264Cyclopropyl(6-phenylpyridin-3-yl)methanol

Procedure

Synthesized using compound 43b (227 mg, 1.24 mmol) and cyclopropylmagnesium bromide (4.96 mL, 2.48 mmol, 0.5 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. Light yellow solid. Yield: 234 mg, 84%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=0.35-0.44 (m, 1H), 0.49 (dq, J=9.4, 4.7 Hz, 1H), 0.55-0.68 (m, 2H), 1.21 (qt, J=8.1, 5.0 Hz, 1H), 3.00 (br, s, 1H), 4.05 (d, J=8.2 Hz, 1H), 7.38-7.44 (m, 1H), 7.44-7.50 (m, 2H), 7.66-7.70 (m, 1H), 7.80-7.85 (m, 1H), 7.94-8.00 (m, 2H), 8.64-8.69 (m, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=2.8, 3.6, 19.0, 75.9, 120.3, 126.8, 128.7, 128.8, 134.5, 137.7, 139.1, 147.6, 156.5; MS (ESI): m/z=226.28 [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-3ce598491a8943429c438fd000adcc39
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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