Thionyl Chloride → HCID 66618955, compound

HRID 406371Notes

Reaction equation

HRID 406371 reaction equation
S(Cl)(Cl)=O.[C:5]([CH2:7][CH2:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:22])([F:21])[F:20])[C:10](O)=[O:11])#[N:6].[BH4-].[Na+]>O1CCCC1.C(O)C>[OH:11][CH2:10][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([F:20])([F:21])[F:22])[CH2:8][CH2:7][C:5]#[N:6]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 4311764Sodium borohydrideHCID 66618946HCID 66618946, compound

Product 1

HCID 66618955HCID 66618955, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Thionyl chloride (8.25 mL) was added to 4-cyano-2-(2-trifluoromethylphenyl)butanoic acid (2.9 g), and the mixture was heated under reflux. After one hour, concentration under reduced pressure gave an oil. The oil was dissolved in tetrahydrofuran (50 mL) and ethanol (20 mL), and sodium borohydride (855 mg) was added at 0° C. After stirring at room temperature for one hour, the reaction was terminated with water, followed by dilution with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid, a saturated sodium bicarbonate aqueous solution and brine and dried over magnesium sulfate. Concentration under reduced pressure gave a pale yellow oil. The oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 50%) to obtain the title compound (2.14 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. concentrationconcentration under reduced pressure
  4. customgave an oil
  5. customthe reaction was terminated with water
  6. washThe organic layer was washed with 1 N hydrochloric acid
  7. dry with materiala saturated sodium bicarbonate aqueous solution and brine and dried over magnesium sulfate
  8. concentrationConcentration under reduced pressure
  9. customgave a pale yellow oil
  10. customThe oil was purified by silica gel column chromatography (mobile phase:ethyl acetate/heptane=0 to 50%)

Sources & evidence

ORD record
ord-4a22a32f54d848fca96f0b063ffedfba
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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