7-Bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde → 5-Formyl-2,3-dihydro-1-benzofuran-7-carbonitrile

HRID 15174

反応式

HRID 15174 の反応式
Br[C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([CH:11]=[O:12])[CH:3]=1.[Cu][C:14]#[N:15]>CC(N(C)C)=O>[CH:11]([C:4]1[CH:3]=[C:2]([C:14]#[N:15])[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=1)=[O:12]

参加物

4

反応物 2

HCID 185261827-Bromo-2,3-dihydro-1-benzofuran-5-carbaldehydeHCID 178418546HCID 178418546、化合物

生成物 1

HCID 574869025-Formyl-2,3-dihydro-1-benzofuran-7-carbonitrile収率 61.4%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

To a solution of 7-bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde (1.3 g, 4.7 mmol) in dimethylacetamide (2 mL) was added copper(I) cyanide (0.41 g g, 4.7 mmol). The reaction was refluxed for 18 h, and then concentrated under reduced pressure. The residue was washed well with warm ethyl acetate. The combined ethyl acetate layer were concentrated and dried. The crude product was purified by flash column chromatography (silica gel, 4:1 and 2:1 hexane:ethyl acetate gradient) to afford the desired product (0.5 g, 50%).

後処理

  1. temperatureThe reaction was refluxed for 18 h
  2. concentrationconcentrated under reduced pressure
  3. washThe residue was washed well with warm ethyl acetate
  4. concentrationThe combined ethyl acetate layer were concentrated
  5. customdried
  6. customThe crude product was purified by flash column chromatography (silica gel, 4:1 and 2:1 hexane:ethyl acetate gradient)

出典と根拠

ORDレコード
ord-5cffa760ea3a42c59d941a8a79d59029
出典データセット
uspto-grants-2010_06
特許番号
US07732460B2

関連ノート

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