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

HRID 356486Notes

Reaction equation

HRID 356486 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](=[O:34])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26]CC3C=CC=CC=3)=[CH:22][CH:21]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H-].[Na+].[C:37](OC)(=[O:42])[CH2:38][C:39]([CH3:41])=[O:40].C([Li])CCC>C1COCC1>[OH:40][C:39]1[CH2:41][C:17]([CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)([CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=2)[O:34][C:37](=[O:42])[CH:38]=1

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 541582871,5-Bis (4-benzyloxy-phenyl)-pentan-3-oneHCID 178418339Butyllithium

Product 1

HCID 546822654-Hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-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 11.2 g (25 mmol) of 1,5-bis (4-benzyloxy-phenyl)-pentan-3-one (prepared in Example H), 1.0 g (25 mmol) of 60% NaH dispersion in mineral oil, 2.88 g (25 mmol) of methyl acetoacetate, 15.6 mL (1.6M, 25 mmol) of n-butyllithium and 300 mL of THF. The reaction mixture was stirred for 12 hours at room temperature, quenched with aqueous NH4Cl, and worked up in the usual manner.

Workup

  1. customquenched with aqueous NH4Cl

Sources & evidence

ORD record
ord-40a37df1d5424bec9c230b2caf42fe52
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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