Methanol → 2-[(Hydroxy)(2-methylpyridin-3-yl)methyl]acrylic acid ethyl ester

HRID 572137Notes

Reaction equation

[CH3:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.C1N2CCN(CC2)C1.CO.[C:20]([O:24][CH2:25][CH3:26])(=[O:23])[CH:21]=[CH2:22]>>[CH2:25]([O:24][C:20](=[O:23])[C:21]([CH:8]([OH:9])[C:7]1[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=1)=[CH2:22])[CH3:26]

Participants

Reactant 4

HCID 887Methanol

HCID 8821Ethyl Acrylate

HCID 9237Dabco

HCID 110838812-Methylpyridine-3-carbaldehyde

Product 1

HCID 666933692-[(Hydroxy)(2-methylpyridin-3-yl)methyl]acrylic acid ethyl esterYield 62%

Conditions

Temperature: 45 °C

Procedure

To 2-methylpyridine-3-carbaldehyde (5 g, 0.04 mol) in ethyl acrylate (10 mL) were added DABCO (1 g, 0.01 mol) and methanol (1 mL). The reaction mixture was stirred at 45° C. for 3 days. The reaction mixture was then concentrated and purified by column chromatography (SiO2, 60-100% EtOAc/DCM) to give the title compound (62%) as a colourless oil. δH (DMSO-d6) 8.32 (dd, J 4.8, 1.7 Hz, 1H), 7.51 (dd, J 7.7, 1.7 Hz, 1H), 7.17 (dd, J 7.7, 4.8 Hz, 1H), 6.28 (t, J 1.3 Hz, 1H), 5.91 (t, J 1.6 Hz, 1H), 5.78 (d, J 5.0 Hz, 1H), 5.62 (d, J 5.0 Hz, 1H), 4.10-4.00 (m, 2H), 3.29 (s, 3H), 1.10 (t, J 7.0 Hz, 3H). LCMS (ES+) 222 (M+H)+, RT 1.11 minutes.

Workup

concentrationThe reaction mixture was then concentrated
custompurified by column chromatography (SiO2, 60-100% EtOAc/DCM)

Sources & evidence

ORD record: ord-b0ad879f74b445e58ec8c81f327155d0
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029392B2

Reaction notes

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