Acetic Acid → HCID 54092388, compound

HRID 1086819Notes

Reaction equation

HRID 1086819 reaction equation
N1CCCCC1.C(O)(=O)C.C[CH:12]([CH3:22])[C:13](=O)[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[CH:23]([C:26](C)=[O:27])([CH3:25])[CH3:24].[F:29][C:30]1C=CC(C=O)=[CH:32][C:31]=1[O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(O)(C)C>[F:29][C:30]1[CH:22]=[CH:12][C:13]([CH:14]=[C:15]([C:26](=[O:27])[CH:23]([CH3:25])[CH3:24])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:32][C:31]=1[O:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8082PiperidineHCID 112513-Methyl-2-butanoneHCID 1100684-Fluoro-3-phenoxybenzaldehydeHCID 12892835Ethyl 5-methyl-4-oxohexanoate

Product 1

HCID 54092388HCID 54092388, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.8 ml (29 mmol) of piperidine and 1.7 ml (29 mmol) of acetic acid are added to a solution of 79 g (0.5 mol) of ethyl 4-methyl-3-oxo-pentanecarboxylate (prepared from methyl isopropyl ketone analogously to the process of S. B. Soloway and F. B. La Forge, J. Am. Chem. Soc. 69, 2677 (1947)) and 108 g (0.5 mol) of 4-fluoro-3-phenoxy-benzaldehyde in 300 ml of isopropanol and stirred overnight at RT. The mixture is then concentrated, the residue is taken up in 500 ml of ether, washed twice with water and once with saturated sodium chloride solution, dried over sodium sulphate and the solvent removed. The residue is distilled under high vacuum until the last fraction passes over at 185° C. and 0.3 mbar. All distillates (44 g) are discarded. The distillation residue contains the product: brownish oil (144.7 g, 81%), which is reacted further without purification. Rf =0.25 (petroleum ether/ethyl acetate 10:1).

Workup

  1. concentrationThe mixture is then concentrated
  2. washwashed twice with water and once with saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. customthe solvent removed
  5. distillationThe residue is distilled under high vacuum until the last fraction passes over at 185° C. and 0.3 mbar
  6. custombrownish oil (144.7 g, 81%), which is reacted further without purification

Sources & evidence

ORD record
ord-e2bd23c1acb14d04acb9dbdf3a9a86fe
Source dataset
uspto-grants-1991_07
Patent number
US05032590

Reaction notes

Loading…