N-Methoxy-N-methylacetamide → 1-[5-(Benzyloxy)pyridin-2-yl]ethan-1-one

HRID 533936

反応式

HRID 533936 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12](Br)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CON(C)[C:19](=[O:21])[CH3:20].[Li]CCCC>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:19](=[O:21])[CH3:20])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 537505N-Methoxy-N-methylacetamideHCID 160946965-(Benzyloxy)-2-bromopyridineHCID 178418339Butyllithium

生成物 1

HCID 231434391-[5-(Benzyloxy)pyridin-2-yl]ethan-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 5-benzyloxy-2-bromo-pyridine (1.0 g), N-methoxy-N-methyl-acetamide (780 mg) and THF (20 mL) under argon at −60° C. was added n-BuLi (2.6 M in toluene, 2.9 mL). After 1 hour the cooling bath was removed. After reaching room temperature the mixture was quenched by addition of saturated NH4Cl-solution. The mixture was distributed between EA and brine. The organic phase was dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography (silica gel, heptane to EA/heptane 3:7) to provide the subtitle compound. MS ESI+: m/z=228 [M+H]+.

後処理

  1. customAfter 1 hour the cooling bath was removed
  2. customAfter reaching room temperature
  3. customwas quenched by addition of saturated NH4Cl-solution
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (silica gel, heptane to EA/heptane 3:7)

出典と根拠

ORDレコード
ord-0ad92eb2b4a949a0b9cee903a9e4631e
出典データセット
uspto-grants-2014_10
特許番号
US08853412B2

関連ノート

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