Ethyl Acetate → 2-(2,4-Dimethyl-phenyl)-malonic acid dimethyl ester

HRID 8599

반응식

HRID 8599 반응식
[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[CH3:17].[CH3:18][C:19](=[O:23])[O:20][CH2:21]C>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:21][O:20][C:19](=[O:23])[CH:18]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[CH3:17])[C:19]([O:20][CH3:21])=[O:23]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 68503Benzene, 1-bromo-2,4-dimethyl-

생성물 1

HCID 688971052-(2,4-Dimethyl-phenyl)-malonic acid dimethyl ester

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

실험 절차

(In analogy to a procedure given in J. Am. Chem. Soc. 122 (2000), 1360–1370.) To a suspension of Pd(OAc)2 (758 mg), 2-(di-tert.-butlylphosphino)-biphenyl (2.02 g) and K3PO4 (65.95 g) in THF (350 ml) dimethylmalonate (21.42 g) and 1-bromo-2,4-dimethyl-benzene (25 g) was added under argon. The mixture was refluxed for 96 h, cooled to rt and diluted with EA (300 ml) and filtered. The filtrate was evaporated and the resulting brown oil was purified on silica gel eluting with heptane:EA 4:1 to 1:1 followed by distillation (bp 95–100° C. at 0.064 mbar) to give 2-(2,4-dimethyl-phenyl)-malonic acid dimethyl ester (5.66 g) as a colourless oil. 1H-NMR(300 MHz, CDCl3): 2.30(s, 6H), 3.75(s, 6H), 4.87(s, 1H), 6.98–7.05(m, 2H), 7.25–7.28(m, 1H).

후처리

  1. additionwas added under argon
  2. temperatureThe mixture was refluxed for 96 h
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe resulting brown oil was purified on silica gel eluting with heptane:EA 4:1 to 1:1
  6. distillationfollowed by distillation (bp 95–100° C. at 0.064 mbar)

출처 및 근거

ORD 기록
ord-82f8576a87f140efbfe729c5f4cccf25
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091201B2

연결된 노트

불러오는 중…