Methyl iodide → HCID 86675235, compound

HRID 1502920Notes

Reaction equation

HRID 1502920 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)([OH:19])[C:15]([F:18])([F:17])[F:16])=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.[H-].[Na+].[CH3:30]I>C1COCC1>[Cl:27][C:22]1[CH:21]=[C:20]([C:14]([O:19][CH3:30])([C:15]([F:18])([F:17])[F:16])/[CH:13]=[CH:12]/[C:9]2[CH:10]=[CH:11][C:6]([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)=[CH:7][CH:8]=2)[CH:25]=[C:24]([Cl:26])[CH:23]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86675234HCID 86675234, compound

Product 1

HCID 86675235HCID 86675235, compoundYield 35.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (E)-4-(4-(1H-1,2,4-triazol-1-yl)phenyl)-2-(3,5-dichlorophenyl)-1,1,1-trifluorobut-3-en-2-ol (0.15 g, 0.36 mmol) in THF (5 mL) was added NaH (60%, 10 mg, 0.44 mmol) at 0° C. The reaction was allowed to stir at 0° C. for 30 min, then methyl iodide (61 mg, 0.44 mmol) was added slowly and the reaction was warmed to ambient temperature and allowed to stir for 4 h. The reaction was quenched with aq NH4Cl solution and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford the title compound as an off-white solid (55 mg, 35%).

Workup

  1. temperaturethe reaction was warmed to ambient temperature
  2. stirringto stir for 4 h
  3. customThe reaction was quenched with aq NH4Cl solution
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-998e81afd29049418fd57ada0d8d97e2
Source dataset
uspto-grants-2015_12
Patent number
US09211280B2

Reaction notes

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