Methane → Methyl 6-benzofurancarboxylate

HRID 2181678ノート

反応式

HRID 2181678 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]#[C:13][Si](C)(C)C)[C:5]([O:7][CH3:8])=[O:6].C>CO.[Cu](I)I>[O:1]1[C:2]2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][C:11]=2[CH:12]=[CH:13]1

参加物

5

反応物 2

HCID 297MethaneHCID 22481756Methyl 3-hydroxy-4-((triMethylsilyl)ethynyl)benzoate

生成物 1

HCID 22481705Methyl 6-benzofurancarboxylate収率 70%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 887Methanol溶媒

反応条件

温度
75 °C

実験手順

Methyl 3-hydroxy-4-[(trimethylsilyl)ethynyl]benzoate (4.15 g, 16.7 mmol) is dissolved in MeOH (45 ml) and treated with DIA (2.34 ml, 16.7 mmol). Copper iodide (159 mg, 0.84 mmol) is added portion-wise and the reaction is heated at 75° C. for 3 h. DARCO (2 g) is added and the reaction is stirred at 95° C. for an additional 2 h, then overnight at RT. The reaction is filtered, concentrated to a brown oil and the crude material is chromatographed over 300 g slurry-packed silica gel, eluting with 10% EtOAc/hexane. The appropriate fractions are collected and concentrated to afford 2.05 g (70%) of methyl 1-benzofuran-6-carboxylate as an orange crystalline solid. 1H NMR (400 MHz, CDCl3) δ 3.97, 6.84, 7.65, 7.78, 7.98, 8.22 ppm.

後処理

  1. additiontreated with DIA (2.34 ml, 16.7 mmol)
  2. customovernight
  3. customat RT
  4. filtrationThe reaction is filtered
  5. concentrationconcentrated to a brown oil
  6. customthe crude material is chromatographed over 300 g slurry-packed silica gel
  7. washeluting with 10% EtOAc/hexane
  8. customThe appropriate fractions are collected
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-e7fecbf52cfb442bb7623cd2f3bcd5ee
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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