Hydrochloric Acid → HCID 86090086, compound

HRID 2100574Notes

Reaction equation

HRID 2100574 reaction equation
[OH:1][CH:2]1[C:10]2[C:5](=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:8][CH:9]=2)[C:4](=[O:15])[O:3]1.[C:16](=O)([O-])[O-].[K+].[K+].IC.Cl>CN(C=O)C.O>[CH:2]([C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:5]=1[C:4]([O:3][CH3:16])=[O:15])=[O:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 161151451(3H)-Isobenzofuranone, 3-hydroxy-7-(trifluoromethyl)-

Product 1

HCID 86090086HCID 86090086, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (±)-3-hydroxy-7-(trifluoromethyl)isobenzofuran-1 (3H)-one, from Example 1, Part B, (3.31 g, 15.2 mmol) in 20 mL of DMF was added potassium carbonate (4.2 g, 30.4 mmol) followed by iodomethane (1.04 mL, 16.7 mmol). The resulting mixture was allowed to stir at ambient temperature for 18 h. The reaction was cooled to 0° C. and carefully acidified with 6N HCl, diluted with water and extracted with EtOAc. The organics were washed with sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 3.1 g (89%) of the title compound which was used without purification. 1H NMR (CDCl3): δ 10.05 (s, 1H), 8.12 (d, 1H, J=7.7 Hz), 7.95 (d, 1H, J=7.7 Hz), 7.76 (t, 1H, J=7.7 Hz), 4.02 (s, 3H).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. extractionextracted with EtOAc
  3. washThe organics were washed with sat'd aq NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered through a pad of silica gel
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea4d2adef6d54524ae34ce1882d758ef
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

Loading…