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

HRID 1417486노트

반응식

HRID 1417486 반응식
[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]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 290120411-Benzyl-1H-indole-4-carbonitrileHCID 178418373HCID 178418373, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a00412a7d9f141e2ab3ffb4f0a258e9c
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05877199

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