Boron trifluoride → HCID 59464315, compound

HRID 1713862Notes

Reaction equation

HRID 1713862 reaction equation
B(F)(F)F.[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1.C(Cl)Cl.[CH2:32](O)[CH2:33][OH:34]>>[CH3:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][C:25]4([O:34][CH2:33][CH2:32][O:28]4)[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 6356Boron trifluorideHCID 59464053HCID 59464053, compoundHCID 86619818HCID 86619818, compound

Product 1

HCID 59464315HCID 59464315, compoundYield 96%

Procedure

Boron trifluoride diethyletherate (3.3 mL, 26.0 mmol) was added dropwise via a syringe to a stirred solution of 4-(4-oxocyclohexyl)phenyl 4-methylbenzenesulphonate (2.49 g, 7.23 mmol) in dry DCM/ethylene glycol (15 mL/14.11 mL) cooled with an isopropanol/ice bath and stirred for 40 minutes. The mixture was poured onto water (50 mL) and extracted with DCM (2×100 mL). The organic phase was washed with 10% sodium hydrogen carbonate solution (100 mL) then dried and concentrated by evaporation to give the title compound (2.685 g, 96%) as a solid; 1H NMR δ 1.54-1.66 (4H, m), 1.68-1.75 (4H, m), 2.43 (3H, s), 2.54-2.60 (1H, m), 3.86-3.89 (4H, s), 6.91-6.95 (2H, m), 7.21-7.25 (2H, m), 7.46-7.48 (2H, m), 7.73-7.75 (2H, m); MS m/e M+Na+ 411.

Workup

  1. temperaturecooled with an isopropanol/ice bath
  2. additionThe mixture was poured onto water (50 mL)
  3. extractionextracted with DCM (2×100 mL)
  4. washThe organic phase was washed with 10% sodium hydrogen carbonate solution (100 mL)
  5. customthen dried
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-18fa7757f90c4b859639a1454c59e55c
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

Loading…