Iodine → 1,6-Dihydro-2,3-dimethyl-6-(4-methylphenyl)-1-phenoxycarbonyl pyridine

HRID 1077841

반응식

HRID 1077841 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Mg].II.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[CH3:19].Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22]>O1CCCC1>[CH3:19][C:13]1[N:12]([C:21]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:22])[CH:17]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)[CH:16]=[CH:15][C:14]=1[CH3:18]

참가 물질

7

반응물 5

HCID 807IodineHCID 78054-BromotolueneHCID 114202,3-LutidineHCID 15891Phenyl chloroformateHCID 5462224Magnesium

생성물 1

HCID 194303781,6-Dihydro-2,3-dimethyl-6-(4-methylphenyl)-1-phenoxycarbonyl pyridine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-60 °C

실험 절차

A solution of p-bromotoluene (13.5 g) in 50 ml of tetrahydrofuran was added to magnesium (1.5 g) and 1 crystal of iodine in a little tetrahydrofuran, and the mixture was refluxed for 1 hour. In a separate flask, a solution of 2,3-lutidine (6.5 g) in 100 ml of tetrahydrofuran was cooled to about -60° C., and the magnesium complex prepared above added, followed by phenyl chloroformate (8 ml). The mixture was stirred for 1 hour at -60° C., then at room temperature overnight. The solvent was removed under reduced pressure, the residue partitioned between ether and 200 ml of 20% ammonium chloride, the organic layer washed with water, followed by dilute hydrochloric acid. The solvent was evaporated under reduced pressure, and the residue flash-chromatographed on silica gel, eluting with 1% ethyl acetate in heptane, to yield 12.4 g of 1,6-dihydro-2,3-dimethyl-6-(4-methylphenyl)-1-phenoxycarbonyl pyridine, m.p. 106° C.

후처리

  1. temperaturethe mixture was refluxed for 1 hour
  2. customthe magnesium complex prepared
  3. additionabove added
  4. customat room temperature
  5. customovernight
  6. customThe solvent was removed under reduced pressure
  7. customthe residue partitioned between ether and 200 ml of 20% ammonium chloride
  8. washthe organic layer washed with water
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue flash-chromatographed on silica gel
  11. washeluting with 1% ethyl acetate in heptane

출처 및 근거

ORD 기록
ord-8c5cc8093e2f499db908a9708aa7c2c0
출처 데이터셋
uspto-grants-1996_08
특허 번호
US05545645

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