Diethyl Ether → 2-Benzyloxy-4-methyl-6-nitrophenyl pyruvic acid ethyl ester

HRID 903917노트

반응식

HRID 903917 반응식
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[CH:4][C:3]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:20]([O:22][C:23](=[O:29])[C:24](OCC)=[O:25])[CH3:21].CCOCC>C(O)(=O)C>[CH2:20]([O:22][C:23](=[O:29])[C:24]([CH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH3:11])=[CH:4][C:3]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:25])[CH3:21]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 7268Diethyl OxalateHCID 20390195(2,5-Dimethyl-3-nitrophenyl)-benzyl ether

생성물 1

HCID 543832372-Benzyloxy-4-methyl-6-nitrophenyl pyruvic acid ethyl ester

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
60 °C

실험 절차

25.7 g of the thus obtained 2,5-dimethyl-3-nitro-O-benzylphenol are added in portions during stirring to a mixture of 17 g freshly prepared potassium-tert.-butylate and 120 ml oxalic acid diethyl ester. After completion of the addition, the mixture is heated to 60° C. for two hours. After cooling, the composition is mixed with 200 ml ether and carefully acidified with diluted acetic acid. The ether phase is washed with neutral water, dried and evaporated. The still present oxalic ester is distilled off in the water jet vacuum at increased bath temperature. The residue is dissolved in ether and the solution is carefully mixed with ligroin. After aspirating and drying, there is obtained 30.6 g (~85° of theory) 2-benzyloxy-4-methyl-6-nitro-phenyl pyruvic acid ethyl ester; m.p. 80°-82° C.

후처리

  1. additionAfter completion of the addition
  2. temperatureAfter cooling
  3. washThe ether phase is washed with neutral water
  4. customdried
  5. customevaporated
  6. distillationThe still present oxalic ester is distilled off in the water jet vacuum
  7. temperatureat increased bath temperature
  8. dissolutionThe residue is dissolved in ether
  9. additionthe solution is carefully mixed with ligroin
  10. customdrying

출처 및 근거

ORD 기록
ord-97885ef0f41344dfb17b3047f74f761f
출처 데이터셋
uspto-grants-1980_10
특허 번호
US04229464

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