Methyl acetoacetate → HCID 54721631, compound

HRID 481859Notes

Reaction equation

HRID 481859 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[Cl:16][C:17]1[CH:18]=[C:19]([CH2:24][CH2:25][C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:27])[CH:20]=[CH:21][C:22]=1[Cl:23]>CCCCCC.O1CCCC1>[Cl:16][C:17]1[CH:18]=[C:19]([CH2:24][CH2:25][C:26]2([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[O:27][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]2)[CH:20]=[CH:21][C:22]=1[Cl:23]

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 13656084HCID 13656084, compoundHCID 178418339Butyllithium

Product 1

HCID 54721631HCID 54721631, 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 1.7 mL of methyl acetoacetate, 630 mg of NaH 60% dispersion in oil, 9.85 mL of 1.6M n-butyl lithium in hexane, 4.0 g of 3-(3,4-dichlorophenyl)propiophenone and 150 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. 145°-147° C.). 1H NMR (CDCl3) δ2.18-2.35 (m, 2H), 2.39-2.50 (m, 1H), 2.68-2.80 (m, 1H), 2.96 (dd, 2H), 3.36 (dd, 2H), 6.90-7.50 (m, 8H).

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-c945245ac98c49ab9f81450a0beb5704
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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