Methyl acetoacetate → HCID 54677018, compound

HRID 356480Notes

Reaction equation

HRID 356480 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])=[CH:11][CH:10]=1)C1C=CC=CC=1.[C:22](OC)(=[O:27])[CH2:23][C:24]([CH3:26])=[O:25].[H-].[Na+].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)([CH:18]([CH3:19])[CH3:20])[O:21][C:22](=[O:27])[CH:23]=1

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 187986371-(4-(Benzyloxy)phenyl)-4-methylpentan-3-oneHCID 178418339Butyllithium

Product 1

HCID 54677018HCID 54677018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared as described in General Method 6 using 40 g (142 mmol) of 1-(4-benzyloxyphenyl)-4-methyl-pentan-3-one (prepared in Example F), 41.2 g (355 mmol) of methyl acetoacetate, 14.2 g (355 mmol) of 60% NaH dispersion in mineral oil, 216 mL (1.64M, 355 mmol) of n-butyllithium and 700 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-6fa0c38099d54175954fe6bdab444d9f
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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