Triethylamine → (E)-tert-butyl 3-(6-methylpyridin-3-yl)acrylate

HRID 657760Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])(=[O:34])[CH:32]=[CH2:33].CCN(CC)CC>CN1C(=O)CCC1.CC([O-])=O.CC([O-])=O.[Pd+2].O>[CH3:8][C:5]1[N:6]=[CH:7][C:2](/[CH:33]=[CH:32]/[C:31]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 5-bromo-2-methylpyridine (5 g, 29.06 mmol) in NMP (60 mL), were added Pd(OAc)2 (0.325 g, 1.45 mmol) and P(o-tol)3 (0.883 g, 2.9 mmol). Subsequently, a solution of tert-butyl acrylate (13.02 g, 101.7 mmol) in Et3N (16.1 mL, 116.2 mmol) was added under N2 to the above mixture and stirred at 90° C. After 16 h, water was added to the reaction mixture and extracted with Et2O (3×). The combined organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo to afford a residue. Purification of the residue by column chromatography (SiO2, 100-200 mesh, Et2O/Pet ether 1:9) afforded the title compound. MS: 220 [M+H]+;

Workup

extractionextracted with Et2O (3×)
dry with materialThe combined organic phase was dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customto afford a residue
customPurification of the residue by column chromatography (SiO2, 100-200 mesh, Et2O/Pet ether 1:9)

Sources & evidence

ORD record: ord-df5f87b9cb4649fa89455e3dfdd1f6b5
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076345B2

Reaction notes

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