2,2,2-Trifluoroethanol → HCID 89514348, compound

HRID 1778572Notes

Reaction equation

HRID 1778572 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](=O)[CH2:6][CH2:7][CH:8]=[CH2:9].[C:11]([N+:15]#[C-])([CH3:14])([CH3:13])[CH3:12].[C:17]([O-:20])(=O)[CH3:18].[NH4+:21].FC(F)(F)[CH2:24][OH:25]>>[C:17]([NH:21][C:5]([CH2:4][CH2:3][CH2:2][Cl:1])([CH2:6][CH2:7][CH:8]=[CH2:9])[C:24]([NH:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:25])(=[O:20])[CH3:18]

Participants

5

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 23577Tert-Butyl isocyanideHCID 517165Ammonium AcetateHCID 55301267HCID 55301267, compound

Product 1

HCID 89514348HCID 89514348, compoundYield 94%

Procedure

A solution of 1-chlorooct-7-en-4-one (1 g, 6.22 mmol), t-butyl isonitrile (2.8 mL, 24.8 mmol) and ammonium acetate 2.8 g (37.3 mmol) in 2,2,2-trifluoroethanol (3 mL), was stirred at room temperature. Once the starting ketone was consumed the reaction was diluted with ethyl acetate, quenched with 2M HCl and extracted with ethyl acetate. The organic extract was washed successively with 2M HCl and saturated aqueous sodium chloride, dried over MgSO4 and concentrated. Purification by column chromatography (ethyl acetate in hexane gave 2-acetamido-N-tert-butyl-2-(3-chloropropyl)hex-5-enamide as yellow oil 1.7 g (94%). ESI MS found for C15H27ClN2O2 m/z [303 (M+1), 325.3 (M+23)].

Workup

  1. customOnce the starting ketone was consumed the reaction
  2. additionwas diluted with ethyl acetate
  3. customquenched with 2M HCl
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed successively with 2M HCl and saturated aqueous sodium chloride
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customPurification by column chromatography (ethyl acetate in hexane

Sources & evidence

ORD record
ord-91522352f2f34a269c9e93a78d97921f
Source dataset
uspto-grants-2016_02
Patent number
US09266908B2

Reaction notes

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