Sodium Cyanide → 2-(2-(4-Fluorophenyl)oxazol-4-yl)-2-hydroxyacetonitrile

HRID 1397394Notes

Reaction equation

HRID 1397394 reaction equation
OP([O-])(O)=O.[K+].[C-:7]#[N:8].[Na+].[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[O:18][CH:19]=[C:20]([CH:22]=[O:23])[N:21]=2)=[CH:13][CH:12]=1>CN(C=O)C.O.O>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[O:18][CH:19]=[C:20]([CH:22]([OH:23])[C:7]#[N:8])[N:21]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 516951Monobasic potassium phosphateHCID 218062352-(4-Fluoro-phenyl)-oxazole-4-carbaldehyde

Product 1

HCID 866749192-(2-(4-Fluorophenyl)oxazol-4-yl)-2-hydroxyacetonitrileYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

KH2PO4 (712 mg, 5.23 mmol) and NaCN (251 mg, 5.12 mmol) were added to a solution of 2-(4-fluorophenyl)oxazole-4-carbaldehyde (500 mg, 2.62 mmol) in DMF-H2O (10 mL, 4:6, v/v). The resulting reaction mixture was stirred at room temperature for 1 h, then diluted with water and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 2-(2-(4-fluorophenyl)oxazol-4-yl)-2-hydroxyacetonitrile (500 mg, yield 87%). 1H NMR (400 MHz, CDCl3) δ 8.07-8.02 (m, 2H), 7.88 (s, 1H), 7.20-7.16 (t, J=8.8 Hz, 2H), 5.62 (s, 1H), 4.38 (br s, 1H). MS (ESI) m/z: Calculated for C11H7FN2O2: 218.05. found: 218.8 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-689c41ec58524280b16f7bb8a9e0b01b
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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