Imidazole → 4-((Tert-butyl(dimethyl)silyl)oxy)-2'-fluoro-5'-methoxybiphenyl-2-yl trifluoromethanesulfonate

HRID 1049589

반응식

HRID 1049589 반응식
[F:1][C:2]([F:24])([F:23])[S:3]([O:6][C:7]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:8]=1[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[F:22])(=[O:5])=[O:4].N1C=CN=C1.[C:30]([Si:34]([CH3:37])([CH3:36])Cl)([CH3:33])([CH3:32])[CH3:31].[Cl-].[NH4+]>CN(C=O)C>[F:24][C:2]([F:23])([F:1])[S:3]([O:6][C:7]1[CH:12]=[C:11]([O:13][Si:34]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:37])[CH3:36])[CH:10]=[CH:9][C:8]=1[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=1[F:22])(=[O:5])=[O:4]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 1177601232'-Fluoro-4-hydroxy-5'-methoxybiphenyl-2-yl trifluoromethanesulfonate

생성물 1

HCID 1317360334-((Tert-butyl(dimethyl)silyl)oxy)-2'-fluoro-5'-methoxybiphenyl-2-yl trifluoromethanesulfonate수율 80%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2′-fluoro-4-hydroxy-5′-methoxybiphenyl-2-yl trifluoromethanesulfonate (2.85 g) and imidazole (800 mg) in DMF (50 mL) was added tert-butyldimethylchlorosilane (1.42 g), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.99 g) as a colorless oil.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-ccb2a4191dca44699145a6059d3a0472
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382188B2

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