Water → HCID 178450084, 화합물

HRID 1368548

반응식

HRID 1368548 반응식
BrC1C=CC2C(=CC=C(OCF)C=2)C=1.[F:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([C:28]([C:33]1[N:34]=[CH:35][N:36](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:37]=1)([OH:32])[CH:29]([CH3:31])[CH3:30])[CH:22]=[CH:21]2.C([Li])CCC.C(C1N=CN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=1)=O.O>CCOCC.CCCCCC.C1COCC1>[F:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([C:28]([C:33]1[N:34]=[CH:35][NH:36][CH:37]=1)([OH:32])[CH:29]([CH3:31])[CH3:30])[CH:22]=[CH:21]2

참가 물질

8

반응물 4

HCID 962WaterHCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 185202081-(6-Fluoromethyloxynaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol 2-Bromo-6-fluoromethyloxynaphthaleneHCID 178418339Butyllithium

생성물 1

HCID 178450084HCID 178450084, 화합물수율 212.7%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-70 °C

실험 절차

Production of 1-(6-Fluoromethyloxynaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol 2-Bromo-6-fluoromethyloxynaphthalene (2.10 g) was dissolved in ether (100 ml), and the solution was cooled to −70° C. To the solution was slowly added a solution of n-butyllithium in hexane (1.6 M, 5.7 ml), and the mixture was stirred at −70° C. for 20 min. To the mixture was added dropwise a solution of 4-formyl-1-trityl-1H-imidazole (1.58 g) in THF (10 ml). The mixture was stirred for 20 min at −70° C. To the mixture was added water, and the mixture was extracted with ethyl acetate and dried. The solvent was distilled off and the residue was purified by silica gel chromatography (eluent, hexane:ethyl acetate=1:1) followed by recrystallization from diisopropyl ether to give the titled compound (1.73 g) as colorless needles.

후처리

  1. stirringThe mixture was stirred for 20 min at −70° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. customdried
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by silica gel chromatography (eluent, hexane:ethyl acetate=1:1)
  6. customfollowed by recrystallization from diisopropyl ether

출처 및 근거

ORD 기록
ord-3393665c27394134946795a64bd73413
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06573289B1

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