Methyl acetoacetate → HCID 54676620, compound

HRID 357831Notes

Reaction equation

HRID 357831 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+:10].C([Li])CCC.[Na+].[C:17]([CH2:25][CH2:26][C:27]([O-:29])=[O:28])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCCCCC.O1CCCC1>[OH:4][C:3]1[CH2:5][C:17]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:24][C:1](=[O:6])[CH:2]=1.[Na+:10].[C:17]([CH2:25][CH2:26][C:27]([O-:29])=[O:28])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydride2×HCID 69836228HCID 69836228, compoundHCID 178418339Butyllithium

Product 2

HCID 54676620HCID 54676620, compoundHCID 69836228HCID 69836228, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent2×

Procedure

The title compound was prepared as described in General Method 1 using 25 mmol of methyl acetoacetate, 27.5 mmol of NaH 60% dispersion in oil, 26.25 mmol of 1.6M n-butyl lithium in hexane in 50 mL of tetrahydrofuran and 25 mmol of 3-benzoylpropionic acid sodium salt in 60 mL of tetrahydrofuran. 3-Benzoylpropionic acid sodium salt was prepared by reacting the acid (25 mmol) with hexane washed NaH (26.25 mmol) in tetrahydrofuran at 0° C. for 30 minutes. The crude product was flash chromatographed using CH2Cl2 /MeOH/CH3CO2H (90/10/0.2) to give a viscous gum. 1H NMR (CDCl3) δ 2.1-2.6 (m, 4 H), 2.9 (d, 1 H), 3.0 (d, 1 H), 3.3 (d, 1 H), 3.4 (d, 1 H), 7.2-7.5 (m, 5 H).

Workup

  1. customchromatographed
  2. customto give a viscous gum

Sources & evidence

ORD record
ord-8c306f9eef7845d8a264a43dc313d154
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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