Methanol → HCID 67453617, compound

HRID 2276773Notes

Reaction equation

HRID 2276773 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, compound

Conditions

Temperature
75 °C

Procedure

To anhydrous methanol (6 mL) at 0° C. under nitrogen was added sodium metal (ca 1 g) and the mixture stirred for 30 min. 1-(6-fluoropyridin-2-yl)cyclobutanecarbonitrile (1.6 g, 9.1 mmol) was then added, and the resulting mixture heated to 75° C. for 45 min. 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 brine, dried over Na2SO4, and concentrated in vacuo to give the desired product (1.7 g) as an 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 brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-19bcc35351f140c2a05efe4dc98414ab
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

Loading…