Methanol → 2-(4-Bromonaphthalen-2-ylmethyl)-5-ethylbenzo[b]thiophene

HRID 550249노트

반응식

HRID 550249 반응식
C([SiH](CC)CC)C.[Br:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([CH:19]([C:21]2[S:25][C:24]3[CH:26]=[CH:27][C:28]([CH2:30][CH3:31])=[CH:29][C:23]=3[CH:22]=2)O)[CH:10]=1.CO.O>C(Cl)Cl>[Br:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([CH2:19][C:21]2[S:25][C:24]3[CH:26]=[CH:27][C:28]([CH2:30][CH3:31])=[CH:29][C:23]=3[CH:22]=2)[CH:10]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 12052TriethylsilaneHCID 67156704(4-Bromo-naphthalen-2-yl)-(5-ethylbenzo[b]-thiophen-2-yl)methanol

생성물 1

HCID 671572602-(4-Bromonaphthalen-2-ylmethyl)-5-ethylbenzo[b]thiophene수율 62%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a nitrogen stream, triethylsilane (0.63 ml, 3.93 mmol) and a boron trifluoride-diethyl ether complex (0.27 ml, 2.16 mmol) were added to a solution of (4-bromo-naphthalen-2-yl)-(5-ethylbenzo[b]-thiophen-2-yl)methanol (780 mg, 1.96 mmol) in methylene chloride (20 ml) at 0° C. and the reaction mixture was stirred at room temperature for three hours. To the obtained solution was added methanol (10 ml) and water (30 ml) and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=n-hexane)] to obtain the title compound (460 mg, 62%).

후처리

  1. extractionthe mixture was extracted with methylene chloride
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. distillationthe solvent was distilled under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [

출처 및 근거

ORD 기록
ord-9f17f36f8de94293bc838e2b0eee9899
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943748B2

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