Potassium Cyanide → 2-(3-Ethoxy-5-ethyl-2-fluorophenyl)-2-hydroxyacetonitrile

HRID 1438159Notes

Reaction equation

HRID 1438159 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([F:14])=[C:6]([CH:9]=[C:10]([CH2:12][CH3:13])[CH:11]=1)[CH:7]=[O:8])[CH3:2].[C-:15]#[N:16].[K+].OS([O-])=O.[Na+]>C(OCC)(=O)C.O>[CH2:1]([O:3][C:4]1[C:5]([F:14])=[C:6]([CH:7]([OH:8])[C:15]#[N:16])[CH:9]=[C:10]([CH2:12][CH3:13])[CH:11]=1)[CH3:2]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 23665763Sodium BisulfiteHCID 579428023-Ethoxy-5-ethyl-2-fluorobenzaldehyde

Product 1

HCID 579428002-(3-Ethoxy-5-ethyl-2-fluorophenyl)-2-hydroxyacetonitrileYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 118D (630 mg, 3.46 mmol) in ethyl acetate (10 mL) was added a solution of KCN (676 mg) and NaHSO3 (1.08 g) dissolved in H2O (10 mL). It was left stirring overnight before extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried and concentrated. The crude producte was purified by column chromatography to give 118E (685 mg, 92% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.23 (t, J=7.69 Hz, 3H) 1.44 (t, J=7.03 Hz, 3H) 2.62 (q, J=7.76 Hz, 2H) 4.11 (q, J=7.03 Hz, 2H) 5.75 (s, 1H) 6.85 (dd, J=7.91, 2.20 Hz, 1H) 6.96 (dd, J=5.93, 1.98 Hz, 1H).

Workup

  1. waitIt was left
  2. extractionbefore extracted with ethyl acetate (2×50 mL)
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customThe crude producte was purified by column chromatography

Sources & evidence

ORD record
ord-a0eeffc992394a29817a723e25642a47
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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