Methyl acetoacetate → HCID 54704707, compound

HRID 481866Notes

Reaction equation

HRID 481866 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][CH2:27][C:28]([O-:30])=[O:29])(=[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][CH2:27][C:28]([OH:30])=[O:29])([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][CH2:27][C:28]([O-:30])=[O:29])(=[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 69836888HCID 69836888, compoundHCID 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 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) δ1.1-1.2 (m, 1H), 1.4-1.6 (m, 1H), 1.8-2.0 (m, 2H), 2.0-2.2 (m, 2H), 2.9 (ABq, 2H), 4.85 (s, 1H), 7.2-7.4 (m, 5H).

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-479bbe2427d9459bb8e25c79451197dc
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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