Benzophenone → 5,6-Dihydro-4-hydroxy-6,6-diphenyl-3-(2-phenylethyl)-2H-pyran-2-one

HRID 357847

反応式

HRID 357847 の反応式
[H-].[Na+].[C:3]1([CH2:9][CH2:10][CH:11]([C:17]([CH3:19])=[O:18])[C:12](OCC)=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([Li])CCC.[C:25]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1.O>[OH:18][C:17]1[CH2:19][C:25]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:32][C:12](=[O:13])[C:11]=1[CH2:10][CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

7

反応物 4

HCID 3102BenzophenoneHCID 24758Sodium hydrideHCID 219459Ethyl 3-oxo-2-(2-phenylethyl)butanoateHCID 178418339Butyllithium

生成物 1

HCID 547217785,6-Dihydro-4-hydroxy-6,6-diphenyl-3-(2-phenylethyl)-2H-pyran-2-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

Alternatively, the title compound could be prepared as follows. A suspension of 0.25 g (6.2 mmol) of sodium hydride in 5 mL of dry THF was cooled to 0° C. under nitrogen and treated with a solution of 1.40 g (6.0 mmol) of ethyl 2-(2-phenylethyl)acetoacetate in THF (2 mL). The solution was stirred at 0° C. for ten minutes, treated with 4.3 mL of 1.4M n-butyllithium, and stirred for another fifteen minutes. A solution of 0.55 g (3.0 mmol) of benzophenone in THF (3 mL) was added all at once, and the reaction mixture was stirred at room temperature for two hours. Water (75 mL) was added, and the mixture was stirred overnight at room temperature. The solution was washed with ether. The aqueous layer was acidified to pH 2 with 6N HCl and extracted with ethyl acetate; the extract was washed with brine, dried over magnesium sulfate, and concentrated. The residue was triturated with ether : hexane 1:1, and the solids were filtered and dried to give the title compound.

後処理

  1. stirringstirred for another fifteen minutes
  2. stirringwas stirred at room temperature for two hours
  3. stirringthe mixture was stirred overnight at room temperature
  4. washThe solution was washed with ether
  5. extractionextracted with ethyl acetate
  6. washthe extract was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was triturated with ether : hexane 1:1
  10. filtrationthe solids were filtered
  11. customdried

出典と根拠

ORDレコード
ord-5579d540face45eba10a64b42e9e279f
出典データセット
uspto-grants-1998_11
特許番号
US05840751

関連ノート

読み込み中…