2,6-Lutidine → 1-(1,3-benzodioxol-5-yl)-2-(6-methyl-2-pyridinyl)Ethanone

HRID 2220060Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C([Li])CCC.CON(C)[C:17]([C:19]1[CH:27]=[CH:26][C:22]2[O:23][CH2:24][O:25][C:21]=2[CH:20]=1)=[O:18]>O1CCCC1>[O:23]1[C:22]2[CH:26]=[CH:27][C:19]([C:17](=[O:18])[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=3)=[CH:20][C:21]=2[O:25][CH2:24]1

Participants

Conditions

Temperature: -60 °C

Procedure

To a −60° C. solution of 2,6-dimethyl pyridine (48 mL, 457 mmol) in tetrahydrofuran (800 mL) was added n-butyl lithium (183 mL, 2.5 M in hexanes, 457 mmol) over 30 minutes. The resulting red solution was stirred at −60° C. for 1 hour, and then treated with a solution of benzo[1,3]dioxole-5-carboxylic acid methoxy-methyl-amide of Step A (415 mmol) in tetrahydrofuran (200 mL) over 1 hour. The resulting reaction mixture was slowly warmed to −20° C. over 3 hours, and then poured over ice (1 kg). The liquid phase was decanted and the ice was washed with methyl tert-butyl ether (1L). The combined organic extracts were washed with saturated aqueous sodium chloride (3×100 mL), dried with magnesium sulfate and concentrated in vacuo to yield the title compound crude (102 g). Recrystallization from toluene yielded the title compound as a yellow solid (57 g, 49% over two steps).

Workup

customThe resulting reaction mixture
temperaturewas slowly warmed to −20° C. over 3 hours
customThe liquid phase was decanted
washthe ice was washed with methyl tert-butyl ether (1L)
washThe combined organic extracts were washed with saturated aqueous sodium chloride (3×100 mL)
dry with materialdried with magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c0cc679c01f24fe0a80c59f725ad25f0
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417041B2

Reaction notes

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