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

HRID 356479

반응식

HRID 356479 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e209b0bc14a640bf9248b15e91816ead
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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