L-Proline → 4-(2-Ethyl-4-hydroxyphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

HRID 512579노트

반응식

HRID 512579 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[O:11][C:10]([CH3:18])([CH3:17])[C:9]2=[O:19])=[C:4]([CH2:20][CH3:21])[CH:3]=1.N1CCC[C@H]1C(O)=[O:25]>[OH-].[Na+].C(OCC)(=O)C.Cl.[Cu]I>[CH2:20]([C:4]1[CH:3]=[C:2]([OH:25])[CH:7]=[CH:6][C:5]=1[CH:8]1[C:9](=[O:19])[C:10]([CH3:18])([CH3:17])[O:11][C:12]([CH3:16])([CH3:15])[C:13]1=[O:14])[CH3:21]

참가 물질

7

반응물 2

HCID 145742L-ProlineHCID 497653874-(4-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

생성물 1

HCID 666775534-(2-Ethyl-4-hydroxyphenyl)-2,2,6,6-tetramethylpyran-3,5-dione

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 313Hydrochloric Acid용매HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
200 °C

실험 절차

A mixture of 4-(4-bromo-2-ethylphenyl)-2,2,6,6,-tetramethylpyran-3,5-dione (1.00 g, 2.8 mmol), copper(I) iodide (0.108 g, 0.57 mmol), and L-proline (0.033 g, 0.28 mmol) in 1M aqueous sodium hydroxide solution (8.8 ml) is heated at 200° C. under microwave irradiation, until the reaction is judged to be complete by LCMS. The mixture is cooled to room temperature, diluted with ethyl acetate and 2 M aqueous hydrochloric acid and filtered through a plug of diatomaceous earth, washing with ethyl acetate. The organic phase is collected, and the aqueous phase is extracted with ethyl acetate. The organic solutions are combined, washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 4-(2-ethyl-4-hydroxyphenyl)-2,2,6,6-tetramethylpyran-3,5-dione.

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationfiltered through a plug of diatomaceous earth
  3. washwashing with ethyl acetate
  4. customThe organic phase is collected
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated under reduced pressure
  10. customThe residue is purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-01f191bebdcf4d66844f7f3b3162164b
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102642B2

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