Methanol → HCID 67453617, compound

HRID 869174Notes

Reaction equation

HRID 869174 reaction equation
[Na].F[C:3]1[N:8]=[C:7]([C:9]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=1.[CH3:15][OH:16]>>[CH3:15][O:16][C:3]1[N:8]=[C:7]([C:9]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 67452252HCID 67452252, compound

Product 1

HCID 67453617HCID 67453617, compoundYield 97%

Conditions

Temperature
75 °C

Procedure

To stirred 6.0 mL of anhydrous methanol at 0° C. under nitrogen was added sodium metal (˜1 g) and the mixture stirred for 30 minutes. To this was added 1-(6-fluoropyridin-2-yl)cyclobutanecarbonitrile (1.6 g, 9.1 mmol) and the resulting mixture heated to 75° C. for 45 minutes. The solution was cooled to room temperature and partitioned between water and EtOAc. The layers were separated, the aqueous phase was extracted with EtOAc, and the combined organic phases were washed with saturated NaCl, dried over Na2SO4 and concentrated in vacuo to give the desired product (1.7 g, 97%) as a colorless oil.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. custompartitioned between water and EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washthe combined organic phases were washed with saturated NaCl
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3d21809c5ec44c1be3d6f0f867dcfb5
Source dataset
uspto-grants-2015_03
Patent number
US08969346B2

Reaction notes

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