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

HRID 512579ノート

反応式

HRID 512579 の反応式
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]

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 313Hydrochloric Acid溶媒HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
200 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-01f191bebdcf4d66844f7f3b3162164b
出典データセット
uspto-grants-2015_08
特許番号
US09102642B2

反応ノート

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