N-Methoxy-N-methylacetamide → HCID 59463280, compound

HRID 1712917Notes

Reaction equation

HRID 1712917 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[CH:7]=1.[Li]CCCC.CON(C)[C:27](=[O:29])[CH3:28]>C(OC)(C)(C)C.O>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][O:9][CH2:8][C:6]2[CH:7]=[C:2]([C:27](=[O:29])[CH3:28])[CH:3]=[N:4][CH:5]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 537505N-Methoxy-N-methylacetamideHCID 59463258HCID 59463258, compoundHCID 178418339Butyllithium

Product 1

HCID 59463280HCID 59463280, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent2×

Procedure

To a solution of 3-bromo-5-{[(4-methoxybenzyl)oxy]methyl}pyridine (4.4 mmol) in methyl t-butyl ether (20 mL) was added n-BuLi (2.5M in hexane, 1.96 mL) dropwise at −78° C. The reaction mixture was allowed to stir for 15 min and then N-methoxy-N-methylacetamide (6.7 mmol) in methyl t-butyl ether (3 mL) was added dropwise. The reaction mixture was allowed to stir for 30 min at −78° C. and then diluted with water and allowed to warm to rt. After stirring for 30 min, the phases were separated and the aqueous solution was extracted with EtOAc. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 1-(5-{[(4-methoxybenzyl)oxy]methyl}pyridin-3-yl)ethanone (3.1 mmol, 70%) as a white solid. LCMS: (FA) ES+ 272.1.

Workup

  1. stirringto stir for 30 min at −78° C.
  2. stirringAfter stirring for 30 min
  3. customthe phases were separated
  4. extractionthe aqueous solution was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-99e8b74bc7be42aabb967724818008e3
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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