Ethyl Indole-3-carboxylate → 1-tert-Butyl 3-ethyl 1H-indole-1,3-dicarboxylate

HRID 863299노트

반응식

HRID 863299 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:2]1.[C:15]([O:19][C:20](=O)[O:21]C(C)(C)C)([CH3:18])([CH3:17])[CH3:16]>CN(C1C=CN=CC=1)C.C(#N)C.C(OCC)(=O)C>[C:15]([O:19][C:20]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:2]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]

참가 물질

6

반응물 2

HCID 247965Ethyl Indole-3-carboxylateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

생성물 1

HCID 539833451-tert-Butyl 3-ethyl 1H-indole-1,3-dicarboxylate수율 105.9%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3.15 g of ethyl indole-3-carboxylate, 4.36 g of di-tert-butylcarbonate and 0.02 g of 4-DMAP in 30 ml of acetonitrile is stirred at room temperature for 15 min. The reaction mixture is then diluted with 200 ml of ethyl acetate. The organic phase is washed with dilute hydrochloric acid, water and saturated sodium chloride solution in succession, dried over sodium sulfate and concentrated. Purification by means of FC over 80 g of silica gel with a 15:1 mixture of hexane and ethyl acetate as the mobile phase gives 5.1 g of the title compound: Rf (G)=0.41.

후처리

  1. washThe organic phase is washed with dilute hydrochloric acid, water and saturated sodium chloride solution in succession
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customPurification by means of FC over 80 g of silica gel
  5. additionwith a 15:1 mixture of hexane and ethyl acetate as the mobile phase

출처 및 근거

ORD 기록
ord-cefa6350b4114ac1b007557d7d94c5d9
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05719141

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