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

HRID 863299ノート

反応式

HRID 863299 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cefa6350b4114ac1b007557d7d94c5d9
出典データセット
uspto-grants-1998_02
特許番号
US05719141

反応ノート

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