2,6-Lutidine → HCID 68885000, compound

HRID 917668Notes

Reaction equation

HRID 917668 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]>C1COCC1>[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

5

Reactant 3

HCID 79372,6-LutidineHCID 10921728N-methoxy-N-methylbenzo[d][1,3]dioxole-5-carboxamideHCID 178418339Butyllithium

Product 1

HCID 68885000HCID 68885000, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-60 °C

Procedure

To a −60° C. of 2,6-dimethyl-pyridine (48.3 mL, 457 mmol, 1.1 equiv) was slowly added n-butyl lithium (183 mL, 2.5 M in hexane, 457 mmol, 1.1 equiv) over 30 minutes. The resulting red solution was stirred at −60° C. for an additional hour, and then treated with a solution of benzo[1,3]dioxole-5-carboxylic acid methoxy-methyl-amide (˜415 mmol) in THF (200 mL) over 1 hour. The reaction was slowly warmed to −20° C. over 3 hours, and then poured into ice (1 kg). The liquid layer was decanted and then washed with brine (3×100 mL), dried over magnesium sulfate, and concentrated in vacuo. Recrystallization from toluene provided 1-Benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)-ethanone (57 g, 54% over two steps).

Workup

  1. customTo a −60° C.
  2. customover 30 minutes
  3. temperatureThe reaction was slowly warmed to −20° C. over 3 hours
  4. customThe liquid layer was decanted
  5. washwashed with brine (3×100 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customRecrystallization from toluene

Sources & evidence

ORD record
ord-89ad61c8083547bca9f4e1db4a08674a
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

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