Methyl acetoacetate → 6-Butyl-5,6-dihydro-4-hydroxy-6-phenyl-2H-pyran-2-one

HRID 481850Notes

Reaction equation

HRID 481850 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[CH2:11]([Li])[CH2:12][CH2:13][CH3:14].[CH3:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>C(C1C=CC=CC=1)(=O)CCCC.O1CCCC1>[CH2:11]([C:8]1([C:18]2[CH:17]=[CH:16][CH:21]=[CH:20][CH:19]=2)[O:7][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]1)[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 8058HexaneHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 546993686-Butyl-5,6-dihydro-4-hydroxy-6-phenyl-2H-pyran-2-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 66093ValerophenoneSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared as described in General Method 1 using 2.7 mL of methyl acetoacetate, 1.1 g of NaH 60% dispersion in oil, 12.5 mL of 2.0M n-butyl lithium in hexane, 5.1 mL of valerophenone and 125 mL of tetrahydrofuran. After addition of the ketone, the reaction was stirred for 10 minutes at 0° C. then allowed to warm to room temperature overnight. The crude product was triturated from diethyl ether to afford a solid (m.p. 124°-126° C.). 1H NMR (CDCl3) δ0.85 (t, 3H), 1.28 (m, 4H), 1.97 (m, 2H), 2.90 (dd, 2H), 3.30 (dd, 2H), 7.28-7.42 (m, 5H).

Workup

  1. temperatureto warm to room temperature overnight
  2. customThe crude product was triturated from diethyl ether

Sources & evidence

ORD record
ord-29591afed28d4ec5b33077c43e89ffc6
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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