Ethyl 4,4,4-trifluoroacetoacetate → HCID 86699744, compound

HRID 515175Notes

Reaction equation

HRID 515175 reaction equation
[N:1]1([C:7]([CH3:12])=[CH:8][C:9](=O)[CH3:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:13][C:14]([F:24])([F:23])[C:15](=O)[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)(=O)C>[CH2:20]([O:19][C:17](=[O:18])[C:16]1[C:15]([C:14]([F:24])([F:23])[F:13])=[CH:12][C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)=[CH:8][C:9]=1[CH3:10])[CH3:21]

Participants

4

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 592427HCID 592427, compound

Product 1

HCID 86699744HCID 86699744, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-morpholin-4-yl-pent-3-en-2-one (2.50 g, 14.8 mmol) and ethyl 4,4,4-trifluoro-3-oxobutanoate (3.0 g, 16.3 mmol) in acetic acid (40 ml) is heated at 120° C. for 3 h. After completion of the reaction (monitored by TLC), the solvent is distilled off, the residue is taken up in water (20 ml) and the pH of the mixture was adjusted to pH=8 with 25% aqueous ammonia. The aqueous layer is extracted with ethyl acetate (2×20 ml) and the combined organic layers are dried over sodium sulfate, evaporated and the crude product is purified by column chromatography (silica gel, 10% ethyl acetate/cyclohexane) to afford 2-methyl-4-morpholin-4-yl-6-(trifluoromethyl)-benzoic acid ethyl ester (1.55 g, 4.89 mmol, 33%).

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. distillationthe solvent is distilled off
  3. extractionThe aqueous layer is extracted with ethyl acetate (2×20 ml)
  4. dry with materialthe combined organic layers are dried over sodium sulfate
  5. customevaporated
  6. customthe crude product is purified by column chromatography (silica gel, 10% ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-c48a830b7d7b42bcb794bc6e119a8c3d
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

Loading…