Hexane → HCID 86669912, compound

HRID 1506451Notes

Reaction equation

HRID 1506451 reaction equation
FC(F)(F)S([O:6][S:7]([C:10]([F:13])([F:12])[F:11])(=[O:9])=[O:8])(=O)=O.[CH3:16][C:17]1[CH:44]=[C:43]2[C:20]([CH2:21][CH2:22][C:23]3[C:24]2=[N:25][O:26][C:27]=3[C:28]2[C:32]([C:33]([F:36])([F:35])[F:34])=[C:31]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[O:30][N:29]=2)=[CH:19][C:18]=1O.CCCCCC>N1C=CC=CC=1>[F:13][C:10]([F:11])([F:12])[S:7]([O:6][C:18]1[CH:19]=[C:20]2[C:43](=[CH:44][C:17]=1[CH3:16])[C:24]1=[N:25][O:26][C:27]([C:28]3[C:32]([C:33]([F:34])([F:35])[F:36])=[C:31]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[O:30][N:29]=3)=[C:23]1[CH2:22][CH2:21]2)(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 8058HexaneHCID 67749Trifluoromethanesulfonic anhydrideHCID 136350296HCID 136350296, compound

Product 1

HCID 86669912HCID 86669912, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoromethanesulfonic anhydride (0.074 mL, 0.440 mmol) was added to a solution of 8-methyl-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-ol (Preparation 64C, 0.121 g, 0.293 mmol) in pyridine (5 mL) at 0° C. over a period of 5 min. The reaction mixture was stirred at 0° C. for ten minutes and then at room temperature overnight. The reaction mixture was concentrated, and the yellowish-brown residue was partitioned between ethyl acetate (10 mL) and water (10 mL). The ethyl acetate layer was washed sequentially with 1N aqueous HCl (10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL). The organic layer was collected, dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography eluting with a mixture of 15% ethyl acetate:85% hexane to yield 8-methyl-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl trifluoromethanesulfonate as a tan solid (0.123 g, 0.226 mmol, 77%). The product had an HPLC ret. time=4.52 min (condition B). LC/MS M+1=545.2.

Workup

  1. customat room temperature
  2. customovernight
  3. concentrationThe reaction mixture was concentrated
  4. customthe yellowish-brown residue was partitioned between ethyl acetate (10 mL) and water (10 mL)
  5. washThe ethyl acetate layer was washed sequentially with 1N aqueous HCl (10 mL), saturated aqueous NaHCO3 (10 mL), and brine (10 mL)
  6. customThe organic layer was collected
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography
  10. washeluting with a mixture of 15% ethyl acetate

Sources & evidence

ORD record
ord-ebe590cb0de14ffba5addd1acc3a7786
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

Loading…