Potassium Cyanide → HCID 57942747, compound

HRID 1438168Notes

Reaction equation

HRID 1438168 reaction equation
[F:1][C:2]([F:15])([O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11])[CH:3]([F:5])[F:4].[C-:16]#[N:17].[K+].OS([O-])=O.[Na+]>C(OCC)(=O)C.O>[OH:11][CH:10]([C:9]1[CH:12]=[CH:13][CH:14]=[C:7]([O:6][C:2]([F:15])([F:1])[CH:3]([F:4])[F:5])[CH:8]=1)[C:16]#[N:17]

Participants

6

Reactant 3

HCID 9032Potassium Cyanide2×HCID 118803Benzaldehyde, 3-(1,1,2,2-tetrafluoroethoxy)-HCID 23665763Sodium Bisulfite2×

Product 1

HCID 57942747HCID 57942747, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To 3-(1,1,2,2-tetrafluoroethoxy)benzaldehyde (222 mg, 1.0 mmol) in ethyl acetate (5 mL) was added a solution of KCN (195 mg, 3.0 mmol) and NaHSO3 (312 mg, 3.0 mmol) dissolved in H2O (10 mL). The reaction was stirred at rt for 8 h. Another portion of KCN (195 mg, 3.0 mmol) and NaHSO3 (312 mg, 3.0 mmol) dissolved in H2O (10 mL) was added. It was left stirring overnight before it was extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried and concentrated to give 130A as an oil. It was used for next step without purification. 1H NMR (400 MHz, CDCl3) δ ppm 5.57 (s, 1H) 5.78-6.04 (m, 1H) 7.28 (d, J=6.15 Hz, 1H) 7.39 (s, 1H) 7.43-7.52 (m, 2H). 19F NMR (376 MHz, CDCl3) δ ppm −136.72, −88.04.

Workup

  1. additionwas added
  2. waitIt was left
  3. stirringstirring overnight before it
  4. extractionwas extracted with ethyl acetate (2×50 mL)
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b3779f3631434d61a2f2eda24926007f
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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