Hydrochloric Acid → 4-(3-Nitrophenyl)-4-oxobutanoic acid

HRID 430721노트

반응식

HRID 430721 반응식
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[N+:14]([C:17]1[CH:18]=[C:19]([C:23](=[O:29])[CH:24]=[CH:25][C:26]([OH:28])=[O:27])[CH:20]=[CH:21][CH:22]=1)([O-:16])=[O:15].Cl>C1COCC1>[N+:14]([C:17]1[CH:18]=[C:19]([C:23](=[O:29])[CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH:20]=[CH:21][CH:22]=1)([O-:16])=[O:15]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 2357513-(3-Nitrobenzoyl)acrylic acidHCID 2724942Triacetoxyborohydride

생성물 1

HCID 2295054-(3-Nitrophenyl)-4-oxobutanoic acid수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of triacetoxyborohydride (Aldrich) (21 g, 10 mmol) in dry THF (220 mL), a solution in dry THF (40 mL) of 4-(3′-nitrophenyl)-4-oxo-2-butenoic acid (2.2 g, 10 mmol)(prepared as described in example 7,(mp. 178-179° C.)), was added on stirring at room temperature, under dry nitrogen atmosphere. The resulting light yellow solution was stirred at room temperature overnight under nitrogen atmosphere. To the colorless reaction mixture, aqueos 1N HCl (50 mL), was slowly added dropwise, on cooling at 0° C. The most of the solvent was evaporated under reduced pressure and the residue taken up with 2N HCl and extracted with the ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated in vacuo, to led to a solid. Recrystallization from diethyl ether/hexane afforded a cream solid (1.7 g ,77%), mp. 162-164° C.

후처리

  1. stirringThe resulting light yellow solution was stirred at room temperature overnight under nitrogen atmosphere
  2. temperatureon cooling at 0° C
  3. customThe most of the solvent was evaporated under reduced pressure
  4. extractionextracted with the ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customRecrystallization from diethyl ether/hexane

출처 및 근거

ORD 기록
ord-3b8c5101edb240ed994b6cceccc46e9e
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323240B1

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