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

HRID 1576663노트

반응식

HRID 1576663 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 8000Boron trifluoride etherate촉매HCID 241Benzene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-96c61b0a6d6a4da080f3aba56dd54138
출처 데이터셋
uspto-grants-1976_09
특허 번호
US03982007

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