Isopropanol → HCID 15676012, compound

HRID 974031Notes

Reaction equation

HRID 974031 reaction equation
[H-].[Na+].[C:3](#[N:5])[CH3:4].C([O:8][C:9](=O)[CH:10]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:14]([F:24])[CH:13]=1)[CH3:11])C.C(O)(C)C>O1CCCC1>[F:24][C:14]1[CH:13]=[C:12]([CH:10]([CH3:11])[C:9](=[O:8])[CH2:4][C:3]#[N:5])[CH:17]=[CH:16][C:15]=1[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 10084622HCID 10084622, compound

Product 1

HCID 15676012HCID 15676012, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

After 60% sodium hydride (6.5 g, 0.163 mmol) was suspended in tetrahydrofuran under nitrogen atmosphere, the mixture was refluxed for 0.5 h, then added dropwise acetonitrile (7.6 g, 0.185 mol) and ethyl-2-(2-fluoro-4-biphenylyl)-propionate described above in tetrahydrofuran (100 ml). After refluxed for 2 h, the mixture was cooled at room temperature and added isopropylalcohol. After stirring for a while, the mixture was evaporated under reduced pressure to a residue, which was made acid with 2N hydrochloric acid and extracted with chloroform. The extracts were washed with water, dried over, and evaporated under reduced pressure to a residue, which was chromatographed and recrystallized with ethanol to afford 4-(2-fluoro-4-biphenylyl)-3-oxo-pentanenitril (18.0 g, 55% yield) as pale yellow crystalline material: mp 84°-85° C.

Workup

  1. temperaturethe mixture was refluxed for 0.5 h
  2. temperatureAfter refluxed for 2 h
  3. customthe mixture was evaporated under reduced pressure to a residue, which
  4. extractionextracted with chloroform
  5. washThe extracts were washed with water
  6. customdried over, and
  7. customevaporated under reduced pressure to a residue, which
  8. customwas chromatographed
  9. customrecrystallized with ethanol

Sources & evidence

ORD record
ord-4a40c65ad37643fe93926f21b77bc9dd
Source dataset
uspto-grants-1991_11
Patent number
US05066666

Reaction notes

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