Ethyl Acetoacetate → HCID 539486, compound

HRID 1908988Notes

Reaction equation

HRID 1908988 reaction equation
[CH2:1](I)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Na].[C:14]([O:20][CH2:21][CH3:22])(=[O:19])[CH2:15][C:16]([CH3:18])=[O:17]>C(O)C>[CH2:1]([CH:15]([C:16]([CH3:18])=[O:17])[C:14]([O:20][CH2:21][CH3:22])=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 20276Undecane, 1-iodo-HCID 5360545Sodium

Product 1

HCID 539486HCID 539486, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(n-undecyl)-acetoacetate was prepared from undecyl iodide (26.6 .g) by reaction with an equivalent amount of the sodium derivative of ethyl acetoacetate in ethanol (5 hours, reflux temperature). After cooling the solvent is removed on a rotary evaporator, 300 ml of hexane is added to the residue, and the precipitate of salt is now easily filtered. The product is of sufficient purity (g.c-m.s.) to dispense with further work-up. Reaction of it (6.80 g) with 3.5-difluoroaniline (3.1 g) and 0.30 g of p-toluenesulfonic acid monohydrate in 100 ml of benzene (water separator, 3 days) produced the anilinocrotonic ester with very little of the starting materials left. After removal of the solvent, the crude product was added quickly to 30 ml of boiling Dowtherm A and kept at boiling temperature for about 10 minutes. The product crystallizes out upon cooling and is isolated by filtration and washing with hexane (50 ml).

Workup

  1. temperatureAfter cooling the solvent
  2. customis removed on a rotary evaporator, 300 ml of hexane
  3. additionis added to the residue
  4. filtrationthe precipitate of salt is now easily filtered
  5. customReaction of it (6.80 g) with 3.5-difluoroaniline (3.1 g) and 0.30 g of p-toluenesulfonic acid monohydrate in 100 ml of benzene (water separator, 3 days)

Sources & evidence

ORD record
ord-03a2a4f2ec674f51a3141882d586c548
Source dataset
uspto-grants-2013_12
Patent number
US08598354B2

Reaction notes

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