Diethyl Ether → 1-(1-Benzyl-1H-indol-4-yl)ethan-1-one

HRID 1417486ノート

反応式

HRID 1417486 の反応式
[CH3:1][Mg]I.[CH2:4]([N:11]1[C:19]2[C:14](=C(C#N)[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl-].[NH4+].C([O:26][CH2:27][CH3:28])C>O1CCCC1>[C:27]([C:28]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[CH:13]=[CH:12][N:11]2[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:26])[CH3:1]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 290120411-Benzyl-1H-indole-4-carbonitrileHCID 178418373HCID 178418373、化合物

生成物 1

HCID 159176701-(1-Benzyl-1H-indol-4-yl)ethan-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

3.3 ml of a 2M solution of methylmagnesium iodide in diethyl ether was added to a mixture of 1.00 g of 1-benzyl-4-cyanoindole (prepared as described in Example 88) in 50 ml of tetrahydrofuran, with ice-cooling, and the reaction mixture was stirred for 1 hour. After this time, a saturated aqueous solution of ammonium chloride was added to the reaction mixture. The aqueous layer was extracted with diethyl ether, and the resulting organic fraction was washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was purified by silica gel column chromatography, using 50 g of silica gel and a 4:1 v/v mixture of hexane and ethyl acetate as the eluent, to yield 1.00 g of the title compound as an oil.

後処理

  1. temperaturecooling
  2. extractionThe aqueous layer was extracted with diethyl ether
  3. washthe resulting organic fraction was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography
  7. additiona 4:1 v/v mixture of hexane and ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-a00412a7d9f141e2ab3ffb4f0a258e9c
出典データセット
uspto-grants-1999_03
特許番号
US05877199

反応ノート

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