Ethyl Acetate → 2-(3,4-Dimethyl-phenyl)-malonic acid dimethyl ester

HRID 8598

반응식

HRID 8598 반응식
[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH3:17])[CH:11]=1.[CH3:18][C:19](=[O:23])[O:20][CH2:21]C>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[CH3:21][O:20][C:19](=[O:23])[CH:18]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH3:17])[CH:11]=1)[C:19]([O:20][CH3:21])=[O:23]

참가 물질

7

반응물 3

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 685044-Bromo-o-xylene

생성물 1

HCID 688978002-(3,4-Dimethyl-phenyl)-malonic acid dimethyl ester

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 27342152-(Di-tert-butylphosphino)biphenyl촉매HCID 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 (455 mg), 2-(di-tert.-butylphosphino)-biphenyl (1.21 g) and K3PO4 (39.6 g) in THF (200 ml) dimethylmalonate (12.85 g) and 1-bromo-3,4-dimethyl-benzene 15.0 g) was added under argon. The mixture was refluxed for 16 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 to give 2-(3,4-dimethyl-phenyl)-malonic acid dimethyl ester (16.2 g) as a colourless oil which slowly crystallises. 1H-NMR (300 MHz, CDCl3): 2.25(s, 3H), 2.26(s, 3H), 3.75(s, 6H), 4.59(s, 1H), 7.10–7.20(m, 3H).

후처리

  1. additionwas added under argon
  2. temperatureThe mixture was refluxed for 16 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

출처 및 근거

ORD 기록
ord-a49db3e4ff1840bf80f49c0406a40f8c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091201B2

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