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

HRID 550228ノート

反応式

HRID 550228 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)]

出典と根拠

ORDレコード
ord-f0fd9f556ab1475b8f1e26d1d0f90cfe
出典データセット
uspto-grants-2011_05
特許番号
US07943748B2

反応ノート

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