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

HRID 430721ノート

反応式

HRID 430721 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 2295054-(3-Nitrophenyl)-4-oxobutanoic acid収率 77%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3b8c5101edb240ed994b6cceccc46e9e
出典データセット
uspto-grants-2001_11
特許番号
US06323240B1

反応ノート

読み込み中…