1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-(tert-Butyl)-3,3-dimethyl-6-nitrobenzofuran-2(3H)-one

HRID 446141

反応式

HRID 446141 の反応式
[C:1]([C:5]1[C:6]([N+:18]([O-:20])=[O:19])=[CH:7][C:8](O)=[C:9]([C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C>C1COCC1>[C:1]([C:5]1[C:6]([N+:18]([O-:20])=[O:19])=[CH:7][C:8]2[O:14][C:12](=[O:13])[C:11]([CH3:16])([CH3:15])[C:9]=2[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 595441502-(5-Tert-butyl-2-hydroxy-4-nitrophenyl)-2-methylpropanoic acid

生成物 1

HCID 595441545-(tert-Butyl)-3,3-dimethyl-6-nitrobenzofuran-2(3H)-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
30 °C

実験手順

To a solution of compound 18 (7.10 g, 25.2 mmol) in 710 mL of anhydrous THF was added EDCI (14.5 g, 75.6 mmol). The resulting suspension was left stirring at 30° C. overnight. The precipitate was filtered and thoroughly washed with DCM. The filtrate was concentrated to dryness and the residue was dissolved in DCM (100 mL). The solution was washed with water (50 mL×2) and brine (50 mL×1). The DCM layer was then dried over anhydrous Na2SO4 and concentrated to give the crude product, which was purified via column chromatography on silica gel (Petroleum ether/EtOAc 200:1→100:1→50:1) to give compound 19 as a white solid. 1H NMR (CDCl3; 400 MHz) δ 7.36 (s), δ 7.10 (s), δ 1.53 (s), δ 1.41 (s).

後処理

  1. waitThe resulting suspension was left
  2. filtrationThe precipitate was filtered
  3. washthoroughly washed with DCM
  4. concentrationThe filtrate was concentrated to dryness
  5. dissolutionthe residue was dissolved in DCM (100 mL)
  6. washThe solution was washed with water (50 mL×2) and brine (50 mL×1)
  7. dry with materialThe DCM layer was then dried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customto give the crude product, which
  10. customwas purified via column chromatography on silica gel (Petroleum ether/EtOAc 200:1→100:1→50:1)

出典と根拠

ORDレコード
ord-f1cbfc004dc74e56b8a9ebbb0701dcac
出典データセット
uspto-grants-2013_07
特許番号
US08476442B2

関連ノート

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