Boron trifluoride etherate → HCID 18662976, compound

HRID 1956185Notes

Reaction equation

HRID 1956185 reaction equation
[CH3:1][C:2]1([CH3:21])[C:10](=O)[C:9]2[C:4](=[C:5]([F:12])[CH:6]=[CH:7][CH:8]=2)[CH:3]1[C:13]1[C:14]([S:19][CH3:20])=[N:15][CH:16]=[N:17][CH:18]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[CH3:1][C:2]1([CH3:21])[CH2:10][C:9]2[C:4](=[C:5]([F:12])[CH:6]=[CH:7][CH:8]=2)[CH:3]1[C:13]1[C:14]([S:19][CH3:20])=[N:15][CH:16]=[N:17][CH:18]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 12052TriethylsilaneHCID 23226991HCID 23226991, compound

Product 1

HCID 18662976HCID 18662976, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 500 mg of 5-(2,2-dimethyl-7-fluoroindan-3-on-1-yl)-4-methylthiopyrimidine, 5.0 g of triethylsilane and 3.0 g of boron trifluoride etherate in 20 mL of 1,2-dichloroethane was heated to reflux with stirring for 16 hr. The resulting solution was cooled and then poured into an aqueous solution of sodium carbonate. The mixture obtained was extracted with ether and the ethereal extract was dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel to obtain a colorless oil. A portion of this oil was crystallized from hexane to obtain 150 mg of the title compound as a white solid melting at 81°-82° C.

Workup

  1. temperatureto reflux
  2. temperatureThe resulting solution was cooled
  3. customThe mixture obtained
  4. extractionwas extracted with ether
  5. extractionthe ethereal extract
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel
  10. customto obtain a colorless oil
  11. customA portion of this oil was crystallized from hexane

Sources & evidence

ORD record
ord-89854b0613a24981ac53c521853d7a3e
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

Loading…