Methyl acetoacetate → 5,6-Dihydro-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

HRID 481855

Reaction equation

HRID 481855 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[H-].[Na+].C([Li])CCC.[C:16]1([CH2:22][CH2:23][C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CCCCCC.O1CCCC1>[C:26]1([C:24]2([CH2:23][CH2:22][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[O:25][C:1](=[O:6])[CH:2]=[CH:3][CH2:5]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 64802DihydrochalconeHCID 178418339Butyllithium

Product 1

HCID 212224185,6-Dihydro-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

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, 25 mmol of 3-phenylpropiophenone and 70 mL of tetrahydrofuran. Upon concentrating the reaction a solid precipitated out which was triturated with ether and filtered (m.p. 130-130.55, °C.). 1H NMR (CDCl3) δ2.2-2.4 (m, 2H), 2.4-2.6 (m, 1H), 2.6-2.8 (m, 1H), 2.9 (d, 1H), 3.0 (d, 1H), 3.3 (d, 1H), 3.4 (d, 1H), 7.0-7.5 (m, 15H).

Workup

  1. concentrationUpon concentrating
  2. customthe reaction a solid
  3. customprecipitated out which
  4. customwas triturated with ether
  5. filtrationfiltered (m.p. 130-130.55, °C.)

Sources & evidence

ORD record
ord-3f136e593d364767b32776b6e13fbf40
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Linked notes

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