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

HRID 550228노트

반응식

HRID 550228 반응식
C([SiH](CC)CC)C.[S:8]1[C:12]([CH:13]([C:15]2[CH:24]=[C:23]([Br:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)O)=[CH:11][C:10]2[CH:26]=[CH:27][CH:28]=[CH:29][C:9]1=2.CO.O>C(Cl)Cl>[Br:25][C:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]([CH2:13][C:12]2[S:8][C:9]3[CH:29]=[CH:28][CH:27]=[CH:26][C:10]=3[CH:11]=2)[CH:24]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 12052TriethylsilaneHCID 67156452(Benzo[b]thiophen-2-yl)-(4-bromo-naphthalen-2-yl)methanol

생성물 1

HCID 671563652-(4-Bromonaphthalen-2-ylmethyl)-benzo[b]thiophene수율 85.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a nitrogen stream, triethylsilane (0.48 ml, 3.01 mmol) and a boron trifluoride-diethyl ether complex (0.34 ml, 2.71 mmol) were added dropwise to a solution of (benzo[b]-thiophen-2-yl)-(4-bromonaphthalen-2-yl)methanol (1.0 g, 2.71 mmol) in methylene chloride (30 mL) at 0° C. The reaction mixture was stirred at room temperature for three hours, and then a 50% methanol aqueous solution (1 ml) was added and further water was added thereto 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=ethyl acetate:n-hexane (1:40)] to obtain the title compound (0.82 g, 85.6%).

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 [developing solution=ethyl acetate:n-hexane (1:40)]

출처 및 근거

ORD 기록
ord-f0fd9f556ab1475b8f1e26d1d0f90cfe
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943748B2

반응 노트

불러오는 중…