Methyl acetoacetate → HCID 54721729, compound

HRID 357804Notes

Reaction equation

HRID 357804 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[CH2:11]([Li])CCC.[CH3:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>C1(C)C=CC(C=O)=CC=1.O1CCCC1>[OH:4][C:3]1[CH2:5][CH:8]([C:18]2[CH:17]=[CH:16][C:21]([CH3:11])=[CH:20][CH:19]=2)[O:7][C:1](=[O:6])[CH:2]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 8058HexaneHCID 24758Sodium hydrideHCID 178418339Butyllithium

Product 1

HCID 54721729HCID 54721729, compound

Reagents, catalysts & solvents 2

HCID 77254-MethylbenzaldehydeSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was prepared as described in General Method 1 using 10 mL of methyl acetoacetate, 3.7 g of NaH 60% dispersion in oil, 58 mL of 1.6M n-butyl lithium in hexane, 10.9 mL of p-tolualdehyde and 250 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 15 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. 138°-139° C.). 1H NMR (CDCl3) δ 2.39 (s, 3 H), 2.93 (dd, 2 H), 3.58 (dd, 2 H), 5.69 (dd, 1 H), 7.23-7.31 (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-112bcc48c32848ceb54e14cc20e3293b
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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