Water → HCID 22018442, 화합물

HRID 1061869

반응식

HRID 1061869 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH:6]=[CH:5]2.C([Li])CCC.[CH:25]([C:28]([C:30]1[N:31]=[CH:32][N:33]([C:35]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=1)=[O:29])([CH3:27])[CH3:26].O>C1COCC1.CCCCCC>[Si:13]([O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:28]([C:30]1[N:31]=[CH:32][N:33]([C:35]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH:34]=1)([OH:29])[CH:25]([CH3:27])[CH3:26])[CH:11]=[CH:10]2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

참가 물질

7

반응물 4

HCID 962WaterHCID 10150490isopropyl(1-trityl-1H-imidazol-4-yl)ketoneHCID 13473083[(6-Bromonaphthalen-2-yl)oxy](tert-butyl)dimethylsilaneHCID 178418339Butyllithium

생성물 1

HCID 22018442HCID 22018442, 화합물수율 90.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-70 °C

실험 절차

6-Bromo-2-tert-butyldimethylsilyloxynaphthalene (60.0 g) was dissolved in THF (600 mL) and the solution was cooled to −70° C. A solution (1.6 M: 111 mL) of n-butyllithium in hexane was slowly added dropwise and the mixture was stirred for 30 min. Then a solution (200 mL) of isopropyl(1-trityl-1H-imidazol-4-yl)ketone (52.1 g) in THF was added dropwise. The mixture was stirred at −70° C. for 30 min. and water was added to stop the reaction. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and saturated brine, dried and concentrated. The residue was recrystallized from ethyl acetate-hexane to give the title compound (79.5 g) as a colorless powder.

후처리

  1. stirringThe mixture was stirred at −70° C. for 30 min.
  2. customthe reaction
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with water and saturated brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was recrystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-40cd567c20ca4a71b9f46177f3f5f678
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960586B2

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