Methyl acetoacetate → HCID 70251287, compound

HRID 356538Notes

Reaction equation

HRID 356538 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])=[CH:10][CH:9]=1)([CH3:4])[CH3:3].[C:22](OC)(=[O:27])[CH2:23][C:24]([CH3:26])=[O:25].[H-].[Na+].C([Li])CCC>C1COCC1>[CH3:4][C:2]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]2([CH:17]([CH3:18])[CH3:19])[CH2:26][C:24]([OH:25])=[CH:23][C:22](=[O:27])[O:20]2)=[CH:12][CH:13]=1)([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 53831644HCID 53831644, compoundHCID 178418339Butyllithium

Product 1

HCID 70251287HCID 70251287, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from [4-(4-methyl-3-oxo-pentyl)-phenyl]-carbamic acid 1,1-dimethylethyl ester obtained in Example PPPPP (2.1 g, 7.2 mmol), methyl acetoacetate (2.1 g, 18.1 mmol), 60% NaH (0.80 g, 20 mmol), and n-butyllithium (14 mL of 1.5M, 21 mmol) in THF as described in General Method 6. The product was carried on crude to the next step.

Sources & evidence

ORD record
ord-875bb18835ad4eaab743fabdc51b87f3
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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