Methyl acetoacetate → HCID 54704707, compound

HRID 357832Notes

Reaction equation

HRID 357832 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+:10].C([Li])CCC.[C:16]([CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CCCCCC.O1CCCC1>[OH:4][C:3]1[CH2:5][C:16]([CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:23][C:1](=[O:6])[CH:2]=1.[Na+:10].[C:16]([CH2:24][CH2:25][CH2:26][C:27]([O-:29])=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydride2×HCID 73914delta-Oxobenzenepentanoic acidHCID 178418339Butyllithium

Product 2

HCID 54704707HCID 54704707, compoundHCID 69836888HCID 69836888, 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 4-benzoylbutyric acid acid sodium salt in 100 mL of tetrahydrofuran. 4-Benzoylbutyric acid sodium salt was prepared by reacting the acid (25 mmol) with hexane washed NaH (17.5 mmol) in tetrahydrofuran at 0° C. for 25 minutes. The crude product was flash chromatographed using CH2Cl2 /MeOH/CH3CO2H (99/1/0.1-97.5/2.5/0.1) to give a solid which was recrystallized from ethyl acetate (m.p. 134°-137° C.). 1H NMR (DMSO-d6) δ 1.1-1.2 (m, 1 H), 1.4-1.6 (m, 1 H), 1.8-2.0 (m, 2 H), 2.0-2.2 (m, 2 H), 2.9 (ABq, 2 H), 4.85 (s, 1 H), 7.2-7.4 (m, 5 H).

Workup

  1. customchromatographed
  2. customto give a solid which
  3. customwas recrystallized from ethyl acetate (m.p. 134°-137° C.)

Sources & evidence

ORD record
ord-41d24d9a7b7c4619a4038c527bd305b3
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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