Methyl acetoacetate → HCID 54721558, compound

HRID 481858Notes

Reaction equation

HRID 481858 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[CH2:16]1[O:24][C:23]2[CH:22]=[CH:21][C:20]([CH2:25][CH2:26][C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:28])=[CH:19][C:18]=2[O:17]1>CCCCCC.O1CCCC1>[O:24]1[C:23]2[CH:22]=[CH:21][C:20]([CH2:25][CH2:26][C:27]3([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[O:28][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]3)=[CH:19][C:18]=2[O:17][CH2:16]1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 1274032HCID 1274032, compoundHCID 178418339Butyllithium

Product 1

HCID 54721558HCID 54721558, 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 0.22 mL of methyl acetoacetate, 90 mg of NaH 60% dispersion in oil, 1 mL of 2.1M n-butyl lithium in hexane, 500 mg of 3-(3,4-methylenedioxyphenyl)propiophenone and 15 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 2 hours. The crude product was triturated from diethyl ether to afford a solid (m.p. 112°-114° C.). 1H NMR (CDCl3) δ2.20-2.28 (m, 2H), 2.37-2.44 (m, 1H), 2.61-2.69 (m, 1H), 2.95 (dd, 2H), 3.32 (dd, 2H), 5.90 (s, 2H), 6.52-6.70 (m, 3H), 7.33-7.44 (m, 5H).

Workup

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

Sources & evidence

ORD record
ord-0b6c12c4ef70461bb021f79b1a1cb6b3
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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