Ethyl Acetoacetate → HCID 54710578, compound

HRID 481868Notes

Reaction equation

HRID 481868 reaction equation
[C:1](OCC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[C:17]([C:25]1[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCCCCC.C(O)(=O)C.O1CCCC1>[OH:4][C:3]1[CH2:5][C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:25]2[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=2)[O:24][C:1](=[O:6])[CH:2]=1

Participants

8

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 267314-BenzoylpyridineHCID 178418339Butyllithium

Product 1

HCID 54710578HCID 54710578, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

The title compound was prepared as described in General Method 1 using 90 mmol of ethyl acetoacetate, 99 mmol of NaH 60% dispersion in oil, 95 mmol of 1.6M n-butyl lithium in hexane and 90 mmol of 4-benzoylpyridine and 250 mL of tetrahydrofuran. The reaction mixture was acidified with acetic acid and the crude solid was washed with ice water (m.p. 148°-150° C.).

Workup

  1. washthe crude solid was washed with ice water (m.p. 148°-150° C.)

Sources & evidence

ORD record
ord-85b5fdc3f7b64076be8afaab44f33e57
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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