Piperidine → HCID 22481729、化合物

HRID 2181655ノート

反応式

HRID 2181655 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1I)[C:5]([O:7][CH3:8])=[O:6].[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[CH2:17][CH3:18])[CH3:14].N1CCCCC1>CN(C=O)C.CCOC(C)=O.[Cu](I)I>[CH2:13]([O:15][CH:16]([O:19][CH2:20][CH3:21])[C:17]1[O:1][C:2]2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][C:11]=2[CH:18]=1)[CH3:14]

参加物

7

反応物 3

HCID 8082PiperidineHCID 20858Propane, 1,1-diethoxy-HCID 10378812Methyl 3-hydroxy-4-iodobenzoate

生成物 1

HCID 22481729HCID 22481729、化合物収率 32.2%

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

A dried flask under nitrogen is charged with methyl 3-hydroxy-4-iodobenzoate (10.0 g, 35.9 mmol), propioaldehyde diethyl acetal (5.72 ml, 40.0 mmol), bistriphenylphosphine palladium diacetate (538 mg, 0.72 mmol), copper iodide (273 mg, 1.4 mmol) and piperidine (3.94 ml, 40.0 mmol) in DMF (50 ml). The mixture is stirred at 45° C. for 6 h, then at RT overnight. The reaction is diluted with EtOAc (250 ml) and washed with 50% saturated 1:1 NaCl/NaHCO3 solution (4×100 ml). The organic layer is dried (Na2SO4), filtered and concentrated to a brown oil. The crude material is chromatographed over 500 g slurry-packed silica, eluting with 15% EtOAc/hexane. The appropriate fractions are collected and concentrated, affording 3.22 g (32%) of methyl 2-(diethoxymethyl)-1-benzofuran-6-carboxylate as an orange oil. 1H NMR (400 MHz, CDCl3): δ 1.29, 3.72, 3.96, 5.70, 6.88, 7.61, 7.95, 8.20 ppm.

後処理

  1. customat RT
  2. customovernight
  3. washwashed with 50% saturated 1:1 NaCl/NaHCO3 solution (4×100 ml)
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a brown oil
  7. customThe crude material is chromatographed over 500 g slurry-packed silica
  8. washeluting with 15% EtOAc/hexane
  9. customThe appropriate fractions are collected
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-4d3df3074ac249668a6cfe8c21477e0e
出典データセット
uspto-grants-2005_05
特許番号
US06894042B2

反応ノート

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