Water → ethyl 1-(methoxymethyl)-7-nitro-1H-indole-2-carboxylate

HRID 1851355노트

반응식

HRID 1851355 반응식
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11]2)([O-:5])=[O:4].[CH3:20][O:21][CH2:22]Cl.O>CN(C)C=O>[CH3:20][O:21][CH2:22][N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[N+:3]([O-:5])=[O:4])[CH:11]=[C:12]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 250407Ethyl 7-nitro-1H-indole-2-carboxylate

생성물 1

HCID 57475941ethyl 1-(methoxymethyl)-7-nitro-1H-indole-2-carboxylate수율 77%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a suspension of sodium hydride (60% in oil, 0.51 g) in N,N-dimethylformamide (15 mL) was slowly added ethyl 7-nitro-1H-indole-2-carboxylate (2.50 g) at 0° C., and the mixture was stirred for 30 min. To the reaction mixture was added chloromethyl methyl ether (1.00 mL) at 0° C. over 20 min, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography and the title compound (2.29 g, yield 77%) was obtained as pale-yellow crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). melting point 62-63° C.

후처리

  1. customat 0° C.
  2. stirringthe mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d2b21aaa24b540bdb255b86191b3370b
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957070B2

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