Dimethylformamide → HCID 71279316, 화합물

HRID 2171023노트

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HRID 2171023 반응식
CS(O[C:6]1([CH2:9][O:10][C:11]2[C:16]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH2:19][CH2:20][C:21]4=[O:26])=[CH:15][CH:14]=[C:13]([O:27][CH3:28])[C:12]=2[O:29][CH3:30])[CH2:8][CH2:7]1)(=O)=O.[N-:31]=[N+:32]=[N-:33].[Na+].[CH3:35]N(C)C=O>>[N:31]([CH2:35][C:6]1([CH2:9][O:10][C:11]2[C:12]([O:29][CH3:30])=[C:13]([O:27][CH3:28])[CH:14]=[CH:15][C:16]=2[C:17]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:18]=2[CH2:19][CH2:20][C:21]3=[O:26])[CH2:7][CH2:8]1)=[N+:32]=[N-:33]

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 86677575HCID 86677575, 화합물

생성물 1

HCID 71279316HCID 71279316, 화합물

실험 절차

To a stirring solution of 1-((2,3-dimethoxy-6-(1-oxo-2,3-dihydro-1H-inden-4-yl)phenoxy)methyl)cyclopropyl methanesulfonate (3 g, 6.72 mmol) in dimethylformamide (20 mL), was added sodium azide (2.18 g, 33.63 mmol) and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was quenched with ice water and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica gel, 0-5% ethyl acetate in pet ether) to afforded 4-(2-((1-(azidomethyl)cyclopropyl)methoxy)-3,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one as a liquid.

후처리

  1. customthe resultant reaction mixture
  2. customThe reaction mixture was quenched with ice water
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography (silica gel, 0-5% ethyl acetate in pet ether)

출처 및 근거

ORD 기록
ord-389b450efeb6417f8023bfdd9f075915
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051290B2

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