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

HRID 356479

Reaction equation

HRID 356479 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e209b0bc14a640bf9248b15e91816ead
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Linked notes

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