Ethyl Acetoacetate → HCID 54721612, compound

HRID 481842Notes

Reaction equation

HRID 481842 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[C:17]1([C:25]2[CH:30]=[CH:29]C=[CH:27][CH:26]=2)[CH:22]=[CH:21][C:20](C=O)=[CH:19][CH:18]=1>CCCCCC.O1CCCC1>[C:25]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:26]=[CH:27][C:9]([CH:8]2[O:7][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]2)=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 24758Sodium hydrideHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 178418339Butyllithium

Product 1

HCID 54721612HCID 54721612, 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 13.0 g of ethyl acetoacetate, 5.3 g of NaH 50% dispersion in oil, 60 mL of 1.6M n-butyl lithium in hexane, 16.3 g of 4-biphenylcarboxaldehyde and 300 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. 150°-152° C.). 'H NMR (CDCl3) δ2.97 (dd, 2H), 3.60 (dd, 2H) 5.77 (dd, 1H), 7.27-7.68 (m, 9H).

Workup

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

Sources & evidence

ORD record
ord-8d0f30c9e4a043029211206d328c0df4
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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