Methyl acetoacetate → HCID 54682294, compound

HRID 1003836Notes

Reaction equation

HRID 1003836 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 (1.64 M, 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-a259bd8ec1484f439700b80419810540
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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