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

HRID 533936

반응식

HRID 533936 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-0ad92eb2b4a949a0b9cee903a9e4631e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853412B2

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