Toluene → HCID 68486125, 화합물

HRID 1191582노트

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HRID 1191582 반응식
[CH3:1][O:2][CH2:3][C:4]1([CH3:14])[C:9](=[O:10])[CH2:8][C:7](=[O:11])[C:6]([CH3:13])([CH3:12])[O:5]1.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cl:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][C:48]([CH2:51][CH3:52])=[C:47]([Pb+3])[CH:46]=2)=[CH:41][CH:40]=1>ClCCl.Cl>[Cl:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]2[CH:50]=[CH:49][C:48]([CH2:51][CH3:52])=[C:47]([CH:8]3[C:7](=[O:11])[C:6]([CH3:13])([CH3:12])[O:5][C:4]([CH2:3][O:2][CH3:1])([CH3:14])[C:9]3=[O:10])[CH:46]=2)=[CH:43][CH:44]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 6212ChloroformHCID 68488092HCID 68488092, 화합물HCID 178476534HCID 178476534, 화합물

생성물 1

HCID 68486125HCID 68486125, 화합물수율 23.9%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매

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온도
80 °C

실험 절차

To a mixture of 2-methoxymethyl-2,6,6-trimethylpyran-3,5-dione (0.141 g, 0.705 mmol) and N,N-dimethylaminopyridine (0.43 g, 3.52 mmol) in a mixed solvent system of anhydrous chloroform (7.5 ml) and anhydrous toluene (1.75 ml), is added 4′-chloro-4-ethylbiphenyl-3-yllead triacetate (0.465 g, 0.775 mmol) in one portion and the mixture heated at 80° C. for 2 hours. The mixture is allowed to cool to room temperature, diluted with dichloromethane and dilute aqueous hydrochloric acid, and stirred for 5 minutes then filtered through diatomaceous earth to remove inorganic residues (additional washing with solvents). The organic fractions are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel (hexane/ethyl acetate 4:1 ratio). Fractions containing the desired product are combined and evaporated in vacuo. Trituration with hexanes affords 4-(4′-chloro-4-ethylbiphenyl-3-yl)-2-methoxymethyl-2,6,6-trimethylpyran-3,5-dione (0.070 g) as a white solid.

후처리

  1. temperatureto cool to room temperature
  2. filtrationthen filtered through diatomaceous earth
  3. customto remove inorganic
  4. washresidues (additional washing with solvents)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated in vacuo
  8. customThe residue is purified by column chromatography on silica gel (hexane/ethyl acetate 4:1 ratio)
  9. additionFractions containing the desired product
  10. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-fe095421815c49c4939072c7f40fdd63
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680012B2

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