Methyl acetoacetate → HCID 54721758, compound

HRID 481845Notes

Reaction equation

HRID 481845 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].C([Li])CCC.[F:16][C:17]([F:27])([F:26])[C:18]1[CH:25]=[CH:24][C:21](C=O)=[CH:20][CH:19]=1>CCCCCC.O1CCCC1>[F:16][C:17]([F:27])([F:26])[C:18]1[CH:25]=[CH:24][C:21]([CH:8]2[O:7][C:1](=[O:6])[CH:2]=[C:3]([OH:4])[CH2:5]2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 679964-(Trifluoromethyl)benzaldehydeHCID 178418339Butyllithium

Product 1

HCID 54721758HCID 54721758, 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 10 mL of methyl acetoacetate, 3.7 g of NaH 60% dispersion in oil, 58 mL of 1.6M n-butyl lithium in hexane, 11.5 g of 4-trifluoromethylbenzaldehyde and 250 mL of tetrahydrofuran. After addition of the aldehyde, the reaction was stirred for 10 minutes at 0° C. then 30 minutes at room temperature. The crude product was triturated from diethyl ether to afford a solid (m.p. 155°-156° C.). 1H NMR (CDCl3) δ2.83 (dd, 1H), 2.99 (dd, 1H), 3.58 (dd, 2H), 5.76 (dd, 1H), 7.50-7.76 (m, 4H).

Workup

  1. custom30 minutes
  2. customat room temperature
  3. customThe crude product was triturated from diethyl ether

Sources & evidence

ORD record
ord-6117e84b7c7b4da6ab7020c02fa0b8b1
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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