Water → (2-Chlorothiophen-3-yl)naphthalen-2-yl Methanol

HRID 34009

反応式

HRID 34009 の反応式
C([Li])CCC.Br[C:7]1[CH:11]=[CH:10][S:9][C:8]=1[Cl:12].[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[CH:23]=[O:24].O>CCCCCC.C(OCC)C>[Cl:12][C:8]1[S:9][CH:10]=[CH:11][C:7]=1[CH:23]([C:14]1[CH:15]=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=1)[OH:24]

参加物

7

反応物 4

HCID 962WaterHCID 62012-NaphthalenecarboxaldehydeHCID 27245593-Bromo-2-chlorothiopheneHCID 178418339Butyllithium

生成物 1

HCID 23070162(2-Chlorothiophen-3-yl)naphthalen-2-yl Methanol収率 84.8%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

実験手順

Under nitrogen atmosphere, to a solution of 3.2 mL of 1.57 M n-butyllithium in hexane in 7 mL of diethyl ether was added a solution of 1.00 g of 3-bromo-2-chlorothiophene in 8 mL diethyl ether at −78° C., and stirred at this temperature for 1 hour. At the same temperature, 0.87 g of 2-naphthaldehyde was added, stirred for 3 hours while raising the temperature to room temperature, then added with water, extracted with ethylacetate, washed successively with saturated aqueous ammonium chloride and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resultant crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:20-1:5), to afford 1.18 g of the title compound as colorless crystals.

後処理

  1. stirringstirred for 3 hours
  2. extractionextracted with ethylacetate
  3. washwashed successively with saturated aqueous ammonium chloride and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe resultant crude product was purified
  7. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:20-1:5)

出典と根拠

ORDレコード
ord-4a80a6305a224c85bee56ea956bdbaea
出典データセット
uspto-grants-2008_09
特許番号
US07429609B2

関連ノート

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