Toluene → HCID 22285063, 화합물

HRID 1061880

반응식

HRID 1061880 반응식
C1(C)C=CC=CC=1.C([Li])CCC.Br[C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C:24]([N:26]([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[O:25])[CH:18]=[CH:17]2.[CH3:33][CH:34]([CH3:61])[C:35]([C:37]1[N:38]=[CH:39][N:40]([C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:41]=1)=[O:36]>CCCCCC.C1COCC1.O>[OH:36][C:35]([C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C:24]([N:26]([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[O:25])[CH:18]=[CH:17]2)([C:37]1[N:38]=[CH:39][N:40]([C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:41]=1)[CH:34]([CH3:61])[CH3:33]

참가 물질

8

반응물 4

HCID 1140TolueneHCID 10150490isopropyl(1-trityl-1H-imidazol-4-yl)ketoneHCID 218796396-bromo-N,N-diisopropyl-2-naphthamideHCID 178418339Butyllithium

생성물 1

HCID 22285063HCID 22285063, 화합물수율 89.6%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

To a solution of toluene (1000 mL) containing a solution (1.6 M : 98.3 mL) of butyllithium in hexane was dropwise added a solution (250 mL) of 6-bromo-N,N-diisopropyl-2-naphthamide (50.0 g) in THF at −70° C. The mixture was stirred at the same temperature for 30 min., and a solution (200 mL) of 2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanone (47.5 g) in THF was added dropwise. The mixture was stirred for 20 min. Water was added and the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated and the residue was recrystallized from isopropyl ether to give the title compound (71.1 g) as a colorless powder.

후처리

  1. stirringThe mixture was stirred for 20 min
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was recrystallized from isopropyl ether

출처 및 근거

ORD 기록
ord-c6d69dfcdc694d08b1f0d374062b7e15
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06960586B2

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