4-Methylpyridine-2-carbaldehyde → 2-(1-Hydroxy-1-cyclopropylmethyl)-4-methyl-pyridine

HRID 1637742Notes

Reaction equation

HRID 1637742 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]=[O:9])[CH:3]=1.[CH:10]1([Mg]Br)[CH2:12][CH2:11]1>>[OH:9][CH:8]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=1)[CH:10]1[CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 100118944-Methylpyridine-2-carbaldehydeHCID 178418630HCID 178418630, compound

Product 1

HCID 187999032-(1-Hydroxy-1-cyclopropylmethyl)-4-methyl-pyridineYield 87%

Procedure

The Grignard reaction of 4-methyl-2-pyridinecarboxaldehyde (1.21 g, 10.0 mmol) and cyclopropylmagnesium bromide (24 ml, 15.0 mmol, 1.5 equiv., 1.6 ml/mmol) provided 1.42 g (87%) of 2-(1-hydroxy-1-cyclopropylmethyl)-4-methyl-pyridine. TLC (silica gel GF): Rf =0.21 acetone-methylene chloride (1:6). 1H NMR (CDCl3,TMS): δ 8.47 (d, 1H, J=5.08 Hz), 7.30 (s, 1H), 7.12 (d, 1H, J=5.14 Hz), 4.70 (brs, 1H), 4.16 (d, 1H, J=7.92 Hz), 2.47 (s, 3H), 1.26-1.12 (m, 1H), 0.74-0.57 (m, 4H). Mass Spectrum: M/Z (relative intensity %): 163 (34), 162 (51), 146 (51), 135 (70), 122 (100), 107 (57), 92 (98).

Sources & evidence

ORD record
ord-5cdf56e0d1cf46f5870e6983eb53f917
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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