Acetic Acid → HCID 23044435, compound

HRID 2165235Notes

Reaction equation

HRID 2165235 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[C-:2].C(N(CC)CC)C.C([O:17][CH:18](O)[C:19]([F:22])([F:21])[F:20])C.C(O)(=O)C>C1C=CC=CC=1>[CH3:7][O:6][C:4]([CH:3]1[CH:18]([C:19]([F:22])([F:21])[F:20])[O:17][CH:2]=[N:1]1)=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 9897Ethanol, 1-ethoxy-2,2,2-trifluoro-HCID 547815Methyl isocyanoacetate

Product 1

HCID 23044435HCID 23044435, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of methyl isocyanoacetate (4.55 ml) and triethylamine (7.0 ml) in benzene (45 ml) was added trifluoroacetaldehyde ethyl hemiacetal (8 ml) at 0° C. The mixture was stirred at room temperature for an hour and then heated with reflux for 2 hours. The resulting mixture was neutrized with acetic acid, evaporated, diluted with ethyl acetate and washed successively with water (2 times), 10% aqueous sodium hydrogen carbonate and brine. After drying over sodium sulfate, the ethyl acetate extract was filtered and concentrated. The residue was distilled (60° C. /4 mmHg) to give 4-methoxycarbonyl-5-trifluoromethyl-2-oxazoline (5 g).

Workup

  1. temperatureheated
  2. temperaturewith reflux for 2 hours
  3. customevaporated
  4. additiondiluted with ethyl acetate
  5. washwashed successively with water (2 times), 10% aqueous sodium hydrogen carbonate and brine
  6. dry with materialAfter drying over sodium sulfate
  7. extractionthe ethyl acetate extract
  8. filtrationwas filtered
  9. concentrationconcentrated
  10. distillationThe residue was distilled (60° C. /4 mmHg)

Sources & evidence

ORD record
ord-7dfb1978bb984aabb5e59bf7776b5ba8
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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