HCID 58495438, compound → HCID 58495580, compound

HRID 1191110Notes

Reaction equation

HRID 1191110 reaction equation
[F:1][C:2]([F:20])([F:19])[CH2:3][S:4][CH2:5][C:6]1([O:18][CH2:17][CH2:16][O:15]1)[C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1>C1COCC1>[F:20][C:2]([F:1])([F:19])[CH2:3][S:4][CH2:5][C:6]1([O:15][CH2:16][CH2:17][O:18]1)[C:7]1[CH:8]=[CH:9][C:10]([CH2:11][NH2:12])=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 58495438HCID 58495438, compound

Product 1

HCID 58495580HCID 58495580, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-[2-(2,2,2-trifluoroethylthio)-1,1-(ethylenedioxy)ethyl]-benzonitrile (248 mg, 0.8 mmol) in anhydrous THF (8 mL) under nitrogen, add borane-tetrahydrofurane complex (9.8 mL, 9.8 mmol) and heat at 60° C. for 3 h. Cool to room temperature and quench with methanol dropwise. Concentrate in vacuo and purify by SCX chromatography to obtain the title compound (250 mg, 99%). MS (ES+) m/z: 308 (M+H)+.

Workup

  1. temperatureCool to room temperature
  2. customquench with methanol dropwise
  3. concentrationConcentrate in vacuo
  4. custompurify by SCX chromatography

Sources & evidence

ORD record
ord-4a1522b56a3b4778a0e41b965ff245ad
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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