Dimethylformamide → HCID 71279316、化合物

HRID 2171023ノート

反応式

HRID 2171023 の反応式
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]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 86677575HCID 86677575、化合物

生成物 1

HCID 71279316HCID 71279316、化合物

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-389b450efeb6417f8023bfdd9f075915
出典データセット
uspto-grants-2015_06
特許番号
US09051290B2

反応ノート

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