Water → HCID 57444530, compound

HRID 860416Notes

Reaction equation

HRID 860416 reaction equation
[C:1]([C:4]([C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1)(C(=O)C)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:3])[CH3:2].C(OCC)(=O)C.O>FC(F)(F)C(O)=O>[C:25]([C:22]1[CH:21]=[CH:20][C:19]([C:18]([CH:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:27])=[CH:24][CH:23]=1)#[N:26]

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 57444529Ethyl 7-acetyl-7-(4-cyanobenzoyl)-8-oxononanoate

Product 1

HCID 57444530HCID 57444530, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
20 °C

Procedure

Ethyl 7-acetyl-7-(4-cyanobenzoyl)-8-oxononanoate (3.5 g) was dissolved in trifluoroacetic acid (12.6 ml) and the mixture was stirred at 20° C. for 15 minutes. The mixture was partitoned between ethyl acetate and water. The organic layer was separated, washed with water, aqueous sodium bicarbonate and brine, dried over MgSO4 (magnesium sulfate), and evaporated to give ethyl 7-(4-cyanobenzoyl)-8-oxononanoate (2.25 g) as an oil.

Workup

  1. customThe organic layer was separated
  2. washwashed with water, aqueous sodium bicarbonate and brine
  3. dry with materialdried over MgSO4 (magnesium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-e00be75486dc4cbcb2c46c3115462fa4
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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