Hydrochloric Acid → HCID 53990204, compound

HRID 399316Notes

Reaction equation

HRID 399316 reaction equation
[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:13][C:14]([F:21])([F:20])[CH2:15][CH2:16][C:17](Cl)=[O:18].Cl>C(OCC)C.C(O)C.C(Cl)(Cl)(Cl)Cl>[CH2:11]([O:10][C:2](=[O:9])[CH:3]([C:17](=[O:18])[CH2:16][CH2:15][C:14]([F:21])([F:20])[F:13])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 5462224MagnesiumHCID 151044744,4,4-Trifluorobutanoyl chloride

Product 1

HCID 53990204HCID 53990204, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
55 °C

Procedure

To a mixture of 20.35 g of magnesium (turning) and 148 ml of ethanol, 0.1 ml of carbon tetrachloride was added and heated to 55° C. To the mixture, a mixed solution of 197 ml of ethanol, 700 ml of diethyl ether and 168 g of diethyl malonate was added dropwise over one hour. After 2 hours, the reaction solution was cooled to -5° C. under a nitrogen flow and 112 g of 4,4, 4-trifluorobutyryl chloride was added. After the temperature was returned to ambient temperature over one hour, the reaction was further conducted for 12 hours. The reaction solution was poured into an aqueous 5% ice-cooled hydrochloric acid, and extracted three times with diethyl ether. The layers were combined and the combined ether layer was washed twice with saturated 20 saline and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to give 179 g of 4,4,4-trifluorobutyryl-malonic acid diethyl ester (b.p.: 125°-134° C., 15 mmHg) (yield: 90%). 1H-NMR (CDCl3, internal standard TMS); δ value (ppm): 1.32 (t, 3H), 2.50 (m, 2H), 2.95 (t, 2H), 4.29 (q, 2H), 4.50 (s, 1H)

Workup

  1. additionwas added
  2. additionwas added
  3. waitAfter the temperature was returned to ambient temperature over one hour
  4. waitthe reaction was further conducted for 12 hours
  5. extractionextracted three times with diethyl ether
  6. washthe combined ether layer was washed twice with saturated 20 saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9ba0a39df6d14c598209720bee10a2b2
Source dataset
uspto-grants-1998_10
Patent number
US05817880

Reaction notes

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