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

HRID 1617301

반응식

HRID 1617301 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
30 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-33b3dc3a41764af289261e9df2c035b2
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765957B2

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