Hydrochloric Acid → 2,3-Dihydro-6-hydroxy-7-methoxy-5-benzofurancarboxaldehyde

HRID 26373

反応式

HRID 26373 の反応式
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][C:4]=1[OH:12].Cl.C[CH2:15][O:16]CC>[C-]#N.[Zn+2].[C-]#N>[OH:12][C:4]1[C:5]([CH:15]=[O:16])=[CH:6][C:7]2[CH2:8][CH2:9][O:10][C:11]=2[C:3]=1[O:2][CH3:1]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 218565712,3-Dihydro-7-methoxy-6-benzofuranol

生成物 1

HCID 218565722,3-Dihydro-6-hydroxy-7-methoxy-5-benzofurancarboxaldehyde

試薬・触媒・溶媒 1

HCID 11186Zinc cyanide (Zn(CN)2)触媒

実験手順

A mixture of 2.49 g. (15 mmole) of 2,3-dihydro-7-methoxy-6-benzofuranol, 5.87 g. (50 mmole) zinc cyanide and 100 ml. of dry ether was saturated with hydrogen chloride for 1 hour at 0°, then for 2 hours at room temperature. The mixture was then allowed to stand overnight at room temperature then concentrated in vacuo and the residue treated with 100 ml. of 0.1N HCl for 1 hour at reflux. After cooling, ether extraction provided the product which was purified by chromatography over silica gel (E. Merck 60), eluting with CHCl3, to yield a colorless solid, m.p. 71°-72°.

後処理

  1. additionA mixture of 2.49 g
  2. waitto stand overnight at room temperature
  3. concentrationthen concentrated in vacuo
  4. additionthe residue treated with 100 ml
  5. temperatureof 0.1N HCl for 1 hour at reflux
  6. temperatureAfter cooling
  7. extractionether extraction
  8. customprovided the product which
  9. customwas purified by chromatography over silica gel (E. Merck 60)
  10. washeluting with CHCl3
  11. customto yield a colorless solid, m.p. 71°-72°

出典と根拠

ORDレコード
ord-976b891d71a945249f1df5c1e41ce565
出典データセット
uspto-grants-1979_04
特許番号
US04150042

関連ノート

読み込み中…