Tetrahydrofuran → HCID 69489493, compound

HRID 1271414Notes

Reaction equation

HRID 1271414 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]([NH2:13])=[O:12])=[CH:5][CH:4]=1.C([O-])(O)=O.[Na+].C1COCC1.[CH2:26]([O:28][C:29](=[O:34])[C:30](=O)[CH2:31]Br)[CH3:27].FC(F)(F)C(OC(=O)C(F)(F)F)=O>>[CH2:26]([O:28][C:29]([C:30]1[N:13]=[C:11]([CH:10]=[CH:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:14])([F:15])[F:1])=[CH:8][CH:7]=2)[O:12][CH:31]=1)=[O:34])[CH3:27]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 9845Trifluoroacetic anhydrideHCID 66144Ethyl bromopyruvateHCID 516892Sodium Bicarbonate2×HCID 27790124-(Trifluoromethyl)-cinnamamide

Product 1

HCID 69489493HCID 69489493, compound

Procedure

To a suspension of 3-(4-trifluoromethyl-phenyl)-acrylamide (5.0 g, 23.2 mmol) and NaHCO3 (7.80 g, 92.9 mmol) in THF (90 ml) 3-bromo-2-oxo-propionic acid ethyl ester (5.53 g, 25.6 mmol) is added under an argon atmosphere. The mixture is heated to reflux for 15 h when another portion of 3-bromo-2-oxo-propionic acid ethyl ester (5.53 g, 25.6 mmol) is added and stirring continued for 5 h. After cooling to r.t. the mixture is filtered, concentrated in vacuo and the resulting residue suspended in THF (20 ml). At 0° C. trifluoroacetic acid anhydride (16.3 g, 77.9 mmol) is added and the mixture stirred at room temperature for 16 h. The mixture is neutralized with sat. NaHCO3, the aqueous layer extracted with ethyl acetate (2×200 ml) and the combined organic phases dried over Na2SO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate/heptane 4:1) yielding 2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazole-4-carboxylic acid ethyl ester as a colorless solid. Yield 5.84 g (81%)

Workup

  1. additionis added under an argon atmosphere
  2. temperatureThe mixture is heated
  3. additionis added
  4. filtrationis filtered
  5. concentrationconcentrated in vacuo
  6. stirringthe mixture stirred at room temperature for 16 h
  7. extractionthe aqueous layer extracted with ethyl acetate (2×200 ml)
  8. dry with materialthe combined organic phases dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe crude product is purified by flash column chromatography (ethyl acetate/heptane 4:1)

Sources & evidence

ORD record
ord-e0529a1f20a34b56960364fd26a3a90c
Source dataset
uspto-grants-2007_04
Patent number
US07205326B2

Reaction notes

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