Diethyl Ether → 4-Acetyl-2-butyl-5-cyano-1-tritylimidazole

HRID 53020

反応式

HRID 53020 の反応式
[CH3:1][Mg]I.[CH2:4]([C:8]1[N:9]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]([C:15]#[N:16])=C(C#N)[N:12]=1)[CH2:5][CH2:6][CH3:7].[Cl-].[NH4+].C([O:40][CH2:41][CH3:42])C>O1CCCC1>[C:41]([C:42]1[N:12]=[C:8]([CH2:4][CH2:5][CH2:6][CH3:7])[N:9]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:10]=1[C:15]#[N:16])(=[O:40])[CH3:1]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 190361382-Butyl-1-tritylimidazole-4,5-dicarbonitrileHCID 178418373HCID 178418373、化合物

生成物 1

HCID 190360854-Acetyl-2-butyl-5-cyano-1-tritylimidazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

11.1 ml of a 2M solution of methylmagnesium iodide in diethyl ether was slowly added dropwise at room temperature, in an atmosphere of nitrogen, to a solution of 4.5 g of 2-butyl-1-tritylimidazole-4,5-dicarbonitrile [prepared as described in step (i) above] in 45 ml of tetrahydrofuran, and the resulting mixture was stirred at room temperature for 3 hours. At the end of this time, a saturated aqueous solution of ammonium chloride was added dropwise, whilst ice-cooling, to the mixture. The tetrahydofuran layer was separated, washed with a saturated aqueous solution of sodium chloride and concentrated by evaporation under reduced pressure to give a concentrate. The aqueous layer was once again extracted with a small amount of ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried and concentrated by evaporation under reduced pressure. The resulting extract was combined with the above concentrate, and the resulting crude product was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, and the product was crystallized from a mixture of ethyl acetate and hexane, to give 1.46 g of the title compound, melting at 159°-160° C. (with decomposition).

後処理

  1. temperaturecooling, to the mixture
  2. customThe tetrahydofuran layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customto give a concentrate
  6. extractionThe aqueous layer was once again extracted with a small amount of ethyl acetate
  7. washThe extract was washed with a saturated aqueous solution of sodium chloride
  8. customdried
  9. concentrationconcentrated by evaporation under reduced pressure
  10. extractionThe resulting extract
  11. customthe resulting crude product was purified by column chromatography through silica gel
  12. additionby volume mixture of hexane and ethyl acetate as the eluent
  13. customthe product was crystallized from a mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-7ee6bbeaf5fb444e93be573abe32d143
出典データセット
uspto-grants-1997_04
特許番号
US05616599

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