Potassium Carbonate → 2-Ethyl-benzofuran-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide

HRID 1357256ノート

反応式

HRID 1357256 の反応式
[Br:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13][N:14]([CH3:28])[C:15]([C:17]1[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[O:19][C:18]=1[CH2:26][CH3:27])=[O:16])=[CH:7]2.Br[CH2:30][C:31]#[N:32].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[C:11]([O:12][CH2:30][C:31]#[N:32])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:13][N:14]([CH3:28])[C:15]([C:17]1[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[O:19][C:18]=1[CH2:26][CH3:27])=[O:16])=[CH:7]2

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 86587386HCID 86587386、化合物

生成物 1

HCID 120835692-Ethyl-benzofuran-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide収率 72%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 2-ethyl-benzofuran-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (0.5 g, 1.14 mmol), prepared in the previous step, bromoacetonitrile (95 μL, 1.36 mmol) and potassium carbonate (0.79 g, 5.7 mmol) in 20 mL of DMF was stirred under nitrogen at room temperature for 18 h (overnight). The reaction was diluted with ethyl acetate and extracted multiple times with water. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give a dark brown oil. The oil was chromatographed on 50 g of silica gel (230-400 mesh) using 5% ethyl acetate in methylene chloride as the eluent. Isolation of the desire component gave 2-ethyl-benzofuran-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (0.39 g, 72%) as a light yellow foam, MS m/z: 477 [M+H]+.

後処理

  1. extractionextracted multiple times with water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customto give a dark brown oil
  5. customThe oil was chromatographed on 50 g of silica gel (230-400 mesh)

出典と根拠

ORDレコード
ord-a0e98bb92d2e47cb846c6161e5fadf89
出典データセット
uspto-grants-2003_07
特許番号
US06589970B2

反応ノート

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