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

HRID 22259

反応式

HRID 22259 の反応式
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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0e92e498393445779a9f494f3924bc02
出典データセット
uspto-grants-1995_06
特許番号
US05428037

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