Methyl acetoacetate → HCID 54721586, compound

HRID 481860Notes

Reaction equation

HRID 481860 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:26])=[CH:19][CH:18]=1>CCCCCC.O1CCCC1>[F:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]2([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[O:26][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]2)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 247261683-(4-Fluorophenyl)-1-phenylpropan-1-oneHCID 178418339Butyllithium

Product 1

HCID 54721586HCID 54721586, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared as described in General Method 1 using 3.1 mL of methyl acetoacetate, 1.2 g of NaH 60% dispersion in oil, 18 mL of 1.6M n-butyl lithium in hexane, 6.0 g of 3-(4-fluorophenyl)propiophenone and 200 mL of tetrahydrofuran. After addition of the ketone, the reaction was stirred for 15 minutes at 0° C. then allowed to warm to room temperature and stirred for 4 hours. The crude product was triturated from diethyl ether to afford a solid (m.p. 155°-157° C.). 1 H NMR (CDCl3) δ2.23-2.29 (m, 2H), 2.42-2.52 (m, 1H), 2.67-2.78 (m, 1H), 2.97 (dd, 2H), 3.35 (dd, 2H), 7.34-7.47 (m, 5H), 6.91-7.07 (m, 4H).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 4 hours
  3. customThe crude product was triturated from diethyl ether

Sources & evidence

ORD record
ord-29d47a65fabb443bbf598c79204cb5f0
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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