5-Nitrofurfural → 2-(4-Benzyloxyphenyl)-3-(5-nitro-2-furyl)acrolein

HRID 1576663ノート

反応式

HRID 1576663 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][O:17]C)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:19]([C:22]1[O:26][C:25]([CH:27]=O)=[CH:24][CH:23]=1)([O-:21])=[O:20]>C1C=CC=CC=1.C(OCC)C.FB(F)F>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[CH:27][C:25]2[O:26][C:22]([N+:19]([O-:21])=[O:20])=[CH:23][CH:24]=2)[CH:16]=[O:17])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 127745-NitrofurfuralHCID 538954501-(4-Benzyloxyphenyl)-2-methoxyethylene

生成物 1

HCID 543039082-(4-Benzyloxyphenyl)-3-(5-nitro-2-furyl)acrolein

試薬・触媒・溶媒 2

HCID 8000Boron trifluoride etherate触媒HCID 241Benzene溶媒2 回

実験手順

6.4 g of 1-(4-benzyloxyphenyl)-2-methoxyethylene, diluted with 10 cc of benzene, are added dropwise at 0°-5° to 11.15 g of 5-nitrofuran-2-aldehyde in 30 cc of dry benzene after the addition of a few drops of diethyl ether/trifluoroborane. The mixture is stirred at 40° for 11/2 hours, is washed with a 5% aqueous sodium acetate solution and with water, dried with magnesium sulphate and concentrated by evaporation. The residue is heated to 90° for 4 hours with 10% hydrochloric acid and glacial acetic acid. The mixture is again concentrated by evaporation, is taken up in ether and the acid salt portion is filtered off. After concentration, orange crystals having a M.P. of 145°-155°, crystallize from the ether solution.

後処理

  1. washis washed with a 5% aqueous sodium acetate solution and with water
  2. dry with materialdried with magnesium sulphate
  3. concentrationconcentrated by evaporation
  4. temperatureThe residue is heated to 90° for 4 hours with 10% hydrochloric acid and glacial acetic acid
  5. concentrationThe mixture is again concentrated by evaporation
  6. filtrationthe acid salt portion is filtered off
  7. concentrationAfter concentration, orange crystals
  8. customcrystallize from the ether solution

出典と根拠

ORDレコード
ord-96c61b0a6d6a4da080f3aba56dd54138
出典データセット
uspto-grants-1976_09
特許番号
US03982007

反応ノート

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