tert-Butyl acrylate → ethyl 1-(2-tert-butoxycarbonylethyl)-4-methyl-1H-indole-2-carboxylate

HRID 355690노트

반응식

HRID 355690 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:6]2.[C:16]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])[CH:17]=[CH2:18].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1>[C:21]([O:20][C:16]([CH2:17][CH2:18][N:6]1[C:7]2[C:3](=[C:2]([CH3:1])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[C:5]1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:19])([CH3:24])([CH3:23])[CH3:22]

참가 물질

5

반응물 3

HCID 15458tert-Butyl acrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 12529972Ethyl 4-methyl-1H-indole-2-carboxylate

생성물 1

HCID 15548944ethyl 1-(2-tert-butoxycarbonylethyl)-4-methyl-1H-indole-2-carboxylate수율 87%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A mixture of ethyl 4-methyl-1H-indole-2-carboxylate (70.0 g, 344 mmol), tert-butyl acrylate (53.0 g, 413 mmol), benzyltrimethylammonium hydroxide (5.76 g, 34.4 mmol) and 1,4-dioxane (1,000 ml) was stirred at 60°-62° C. for 8.5 hours. The solvent was distilled off under reduced pressure and water (1,000 ml) and acetic acid (30 ml) were added to the residue, followed by extraction with ethyl acetate (twice). The extract solution was washed with a 5% aqueous sodium hydrogencarbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was crystallized from isopropanol (230 ml) to obtain ethyl 1-(2-tert-butoxycarbonylethyl)-4-methyl-1H-indole-2-carboxylate (99.2 g). M.p. 78°-79° C.

후처리

  1. distillationThe solvent was distilled off under reduced pressure and water (1,000 ml) and acetic acid (30 ml)
  2. additionwere added to the residue
  3. extractionfollowed by extraction with ethyl acetate (twice)
  4. washThe extract solution was washed with a 5% aqueous sodium hydrogencarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was crystallized from isopropanol (230 ml)

출처 및 근거

ORD 기록
ord-a6f7c0451dee44a0a263b7172008d5dd
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834454

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