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Triphenylphosphine → N-(6-Formyl-4-methylpyridin-2-YL)acetamide

HRID 505432
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HRID 505432 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH:8]=C)[N:5]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:3]=1.[O:14]=[O+][O-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CO.ClCCl>[CH:8]([C:6]1[N:5]=[C:4]([NH:10][C:11](=[O:13])[CH3:12])[CH:3]=[C:2]([CH3:1])[CH:7]=1)=[O:14]
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참가 물질

6

반응물 3

HCID 11776TriphenylphosphineHCID 24823Ozone3회HCID 68461930N-(4-Methyl-6-vinyl-pyridin-2-yl)-acetamide2회

생성물 1

HCID 72214398N-(6-Formyl-4-methylpyridin-2-YL)acetamide

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

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온도
-80 °C

실험 절차

5.0 g N-(4-methyl-6-vinyl-pyridin-2-yl)-acetamide (compound F5) are dissolved in a mixture of each 200 ml methanol and dichloromethane and cooled to −80° C. Subsequently, ozone is passed into the solution (flow 20-25 l/h ozone). After 5 min ozone treatment is stopped. Thereafter, nitrogen is applied for 5 min and 7.44 g of triphenylphosphane are added while stirring is continued. The solution is allowed to warm up to r.t. Subsequently, the volatile components are removed in vacuo and the residue is purified by chromatography on silica gel (eluent cyclohexane/ethyl acetate 3:1) to afford 2.72 g of the title compound as colourless solid. M.p. 202° C. GC-MS: 178.2 (M+). TLC: Rf=0.50 (cyclohexane/ethyl acetate 1:1). [Remark: Occasionally remaining traces of triphenylphosphine oxide can be removed by dissolving crude product in ethyl acetate followed by cooling to precipitate triphenylphosphine oxide.]

후처리

  1. temperatureto warm up to r.t
  2. customSubsequently, the volatile components are removed in vacuo
  3. customthe residue is purified by chromatography on silica gel (eluent cyclohexane/ethyl acetate 3:1)

출처 및 근거

ORD 기록
ord-a4433b800bab4e53b6cb7cd884cc860b
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07781453B2

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