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

HRID 356490Notes

Reaction equation

HRID 356490 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.C([Si](C)(C)[O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:31])=[CH:24][CH:23]=1)(C)(C)C>C1COCC1>[OH:4][C:3]1[CH2:5][C:30]([CH2:29][CH2:28][C:25]2[CH:24]=[CH:23][C:22]([OH:21])=[CH:27][CH:26]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[O:31][C:1](=[O:6])[CH:2]=1

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 187987033-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-1-phenyl-propan-1-oneHCID 178418339Butyllithium

Product 1

HCID 546822874-Hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-phenyl-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 4.3 mL (40 mmol) of methyl acetoacetate, 1.64 g (41 mmol) of 60% sodium hydride, 25.6 mL (41 mmol) of 1.6M n-butyllithium, 6.81 g (20 mmol) of 3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1-phenyl-propan-1-one (from Example P) and 200 mL of THF. The product was carried on crude to the next step.

Sources & evidence

ORD record
ord-c5c545276f5e43a79a52ae6d8a07fb86
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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