Sodium Cyanide → HCID 68294666, compound

HRID 2279532Notes

Reaction equation

HRID 2279532 reaction equation
Br[CH2:2][C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[C:7]([F:15])[CH:6]=1)[OH:4].[C-:16]#[N:17].[Na+]>CCO.O>[F:15][C:7]1[CH:6]=[C:5]([C@@H:3]([OH:4])[CH2:2][C:16]#[N:17])[CH:10]=[CH:9][C:8]=1[C:11]([F:14])([F:13])[F:12]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86705523HCID 86705523, compound

Product 1

HCID 68294666HCID 68294666, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 258 (0.8 g, 2.8 mmol) and EtOH:water (4:1) was heated to 50° C. was added NaCN (0.20 g, 4.2 mmol) and the reaction stirred at 50° C. overnight. The reaction was then cooled and concentrated to dryness then partitioned between H2O and EtOAc. The combined organic fractions were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (4:1 to 3:1) to afford 0.5 g (77%) of (S)-3-(3-fluoro-4-(trifluoromethyl)phenyl)-3-hydroxypropanenitrile (282).

Workup

  1. temperatureThe reaction was then cooled
  2. concentrationconcentrated to dryness
  3. customthen partitioned between H2O and EtOAc
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with a hexane/EtOAc gradient (4:1 to 3:1)

Sources & evidence

ORD record
ord-4f71b363e8fb42f88ed3b43293459b95
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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