Dimethylformamide dimethyl acetal → HCID 86662869, compound

HRID 1483810Notes

Reaction equation

HRID 1483810 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1.CCN(C(C)C)C(C)C.CO[CH:26](OC)[N:27]([CH3:29])[CH3:28]>>[CH3:29][N:27]([CH3:28])[CH:26]=[C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:1])([F:13])[F:14])[CH:5]=1)[C:11]#[N:12]

Participants

4

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 81531DiisopropylethylamineHCID 5179063-(Trifluoromethoxy)phenylacetonitrile

Product 1

HCID 86662869HCID 86662869, compoundYield 72%

Procedure

A mixture of 3-trifluoromethoxyphenylacetonitrile (2.5 grams, 12.43 mmol), DIPEA (0.321 grams, 2.48 mmol), and dimethyl formamide dimethyl acetal (20 mL) were heated at reflux for 4 h. On cooling, the reaction was partitioned between EtOAc and saturated aqueous NH4Cl solution. The aqueous phase was extracted with ethyl acetate and the combined organic phase washed with brine and concentrated in vacuo. The crude product was purified by chromatography (ethyl acetate/hexane, 0-10%) on silica gel (24 grams) to give pure product (2.3 grams, 8.98 mmol, 72% yield.).

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 4 h
  3. temperatureOn cooling
  4. customthe reaction was partitioned between EtOAc and saturated aqueous NH4Cl solution
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic phase washed with brine
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography (ethyl acetate/hexane, 0-10%) on silica gel (24 grams)
  9. customto give pure product (2.3 grams, 8.98 mmol, 72% yield.)

Sources & evidence

ORD record
ord-7e11d1d1871f4df89f203fb5a3b65e82
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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