Dimethylformamide → 5-Chloro-4-hydroxymethylthiophene-2-carbonitrile

HRID 34072ノート

反応式

HRID 34072 の反応式
Br[C:2]1[S:6][C:5]([Cl:7])=[C:4]([CH2:8][OH:9])[CH:3]=1.[CH3:10][N:11](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:7][C:5]1[S:6][C:2]([C:10]#[N:11])=[CH:3][C:4]=1[CH2:8][OH:9]

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 23070160(5-Bromo-2-chlorothiophen-3-yl)methanol

生成物 1

HCID 230701655-Chloro-4-hydroxymethylthiophene-2-carbonitrile

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a solution of 25.0 g (5-bromo-2-chlorothiophen-3-yl)methanol in 330 mL of dimethylformamide, 25.8 g of zinc cyanide (I) and 12.7 g tetrakis(triphenylphosphine)palladium(0) were added at room temperature, and stirred at 100° C. for 4 hours. Diluting with ethyl acetate, the organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:5), to afford 16.0 g of the title compound as colorless crystals.

後処理

  1. washthe organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe crude product was purified
  5. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:5)

出典と根拠

ORDレコード
ord-fe53eddbf6e24573b0d61b6749f23191
出典データセット
uspto-grants-2008_09
特許番号
US07429609B2

反応ノート

読み込み中…