Methyl acetoacetate → HCID 54721549, compound

HRID 357814Notes

Reaction equation

HRID 357814 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]CCC>CC1C=C(C=CC=1)C=O.O1CCCC1>[OH:4][C:3]1[CH2:5][CH:8]([C:11]2[CH:18]=[CH:17][CH:16]=[C:13]([CH3:14])[CH:12]=2)[O:7][C:1](=[O:6])[CH:2]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 8058HexaneHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 54721549HCID 54721549, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 121053-MethylbenzaldehydeSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared as described in General Method 1 using 2.0 mL of methyl acetoacetate, 0.8 g of NaH 60% dispersion in oil, 10 mL of 2.0M n-butyl lithium in hexane, 2.6 mL of 3-methylbenzaldehyde and 100 mL of tetrahydrofuran. After addition of the aldehyde, 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. 137°-138° C.). 1H NMR (CDCl3) δ 2.38 (s, 3 H), 2.88 (dd, 1 H), 2.95 (dd, 1 H), 3.57 (dd, 2 H), 5.68 (dd, 1 H), 7.16-7.33 (m, 4 H).

Workup

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

Sources & evidence

ORD record
ord-3160fa2805b64ea58d04227378d1c872
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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