Methyl acetoacetate → HCID 54682294, compound

HRID 356482Notes

Reaction equation

HRID 356482 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]C(=O)CCCC)=[CH:11][CH:10]=1)C1C=CC=CC=1.[C:23]([O:29][CH3:30])(=[O:28])[CH2:24][C:25]([CH3:27])=[O:26].[H-].[Na+].[CH2:33]([Li])[CH2:34][CH2:35][CH3:36]>C1COCC1>[CH2:33]([C:30]1([CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[O:29][C:23](=[O:28])[CH:24]=[C:25]([OH:26])[CH2:27]1)[CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 187986701-(4-Benzyloxyphenyl)-heptan-3-oneHCID 178418339Butyllithium

Product 1

HCID 54682294HCID 54682294, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according the General Method 6 using 4.0 g (13 mmol) of 1-(4-benzyloxyphenyl)-heptan-3-one (prepared in Example U), 6.3 g (54 mmol) of methyl acetoacetate, 2.2 g (54 mmol) of 60% NaH dispersion in mineral oil, 33 mL (1.64M, 54 mmol) of n-butyllithium and 110 mL of THF. The reaction mixture was quenched with 0.1 NH4Cl, and the mixture was worked up in the normal fashion.

Workup

  1. customThe reaction mixture was quenched with 0.1 NH4Cl

Sources & evidence

ORD record
ord-96e32938c83d4a1ab80f23cd624a7469
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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