1-Butanol → HCID 44236584, compound

HRID 1503192Notes

Reaction equation

HRID 1503192 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[CH2:9][C:10]#[N:11])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([OH:23])CCC.[OH-].[K+]>Cl>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[CH2:9][C:10]([NH2:11])=[O:23])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 14797Potassium HydroxideHCID 58155370HCID 58155370, compound

Product 1

HCID 44236584HCID 44236584, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3-(2-fluoro-biphenyl-4-yl)butyronitrile in tent-butyl alcohol was added 1.87 g of finely powdered potassium hydroxide. The resulting suspension was stirred and heated to 70° C. for 2.5 hours and cooled to room temperature. The reaction suspension was diluted with 1.0 N HCl solution (100 mL) and extracted with ethyl acetate (2×100 mL). The ethyl acetate extracts were combined and washed with 5% bicarbonate solution (100 mL) and then with H2O (100 mL). The organics were then dried over MgSO4, and concentrated to a white solid which was re-crystallized several times with EtOAc/Hex to give white flaky prisms (1.62 g, 75% yield).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washwashed with 5% bicarbonate solution (100 mL)
  4. dry with materialThe organics were then dried over MgSO4
  5. concentrationconcentrated to a white solid which
  6. customwas re-crystallized several times with EtOAc/Hex

Sources & evidence

ORD record
ord-8d2c0e3cba8c4e87bde366eff6d826d1
Source dataset
uspto-grants-2015_12
Patent number
US09212155B2

Reaction notes

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