Methyl acetoacetate → 4-Hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-methyl-5,6-dihydro-pyran-2-one

HRID 356479

反応式

HRID 356479 の反応式
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](=[O:19])[CH3:18])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[H-].[Na+].[C:22](OC)(=[O:27])[CH2:23][C:24]([CH3:26])=[O:25].C([Li])CCC>C1COCC1>[OH:25][C:24]1[CH2:26][C:17]([CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)([CH3:18])[O:19][C:22](=[O:27])[CH:23]=1

参加物

6

反応物 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 187986664-(4-tert-Butyldimethylsilyloxy-phenyl)-2-butanoneHCID 178418339Butyllithium

生成物 1

HCID 546822784-Hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-methyl-5,6-dihydro-pyran-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The title compound was prepared as described in General Method 6 using 16.9 g (60.9 mmol) of 4-(4-tert-butyldimethylsilyloxyphenyl)-2-butanone (prepared in Example R), 7.32 g (183 mmol) of 60% NaH dispersion in mineral oil, 21.2 g (183 mmol) of methyl acetoacetate, 114 mL (1.64M, 183 mmol) of n-butyllithium and 360 mL of THF. The reaction mixture was quenched with 0.1N HCl and the product was extracted into EtOAc. The organic layer was dried (MgSO4) and the solvents were evaporated.

後処理

  1. customThe reaction mixture was quenched with 0.1N HCl
  2. extractionthe product was extracted into EtOAc
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvents were evaporated

出典と根拠

ORDレコード
ord-e209b0bc14a640bf9248b15e91816ead
出典データセット
uspto-grants-1998_11
特許番号
US05834506

関連ノート

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