Tetrahydrofuran → 3-(3-Phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde

HRID 1506329Notes

Reaction equation

HRID 1506329 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]3[O:20][N:19]=[C:18]4[C:21]5[C:26]([CH2:27][CH2:28][C:17]=34)=[CH:25][C:24]([CH:29]=C)=[CH:23][CH:22]=5)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C[O:34]CC1.C[N+]1([O-])CCOCC1.I([O-])(=O)(=O)=O.[Na+]>O.[Os](=O)(=O)(=O)=O>[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]3[O:20][N:19]=[C:18]4[C:21]5[C:26]([CH2:27][CH2:28][C:17]=34)=[CH:25][C:24]([CH:29]=[O:34])=[CH:23][CH:22]=5)[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 671720363-(3-Phenyl-4-(trifluoromethyl)isoxazol-5-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

Product 1

HCID 866698763-(3-Phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehydeYield 98%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

To a stirred mixture of 3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (7A, 1.96 g, 4.80 mmol) and THF (20 mL) were added NMO (50% in water, 1.493 mL, 7.20 mmol) and osmium tetroxide (4% in water, 1.173 mL, 0.192 mmol) at room temperature. The mixture was vigorously stirred at room temperature overnight. A solution of sodium periodate (1.540 g, 7.20 mmol) in water (10 mL) was added. The mixture was stirred at room temperature under nitrogen for 30 min. Water (20 mL) was then added. The solid was filtered, washed with water (2×5 mL) and ethanol (2 mL) and dried to give 3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde (1.92 g, 4.68 mmol, 98%) as a white solid. The compound had an HPLC retention time=3.95 min (condition C); LC/MS M+1=410.9.

Workup

  1. stirringThe mixture was stirred at room temperature under nitrogen for 30 min
  2. filtrationThe solid was filtered
  3. washwashed with water (2×5 mL) and ethanol (2 mL)
  4. customdried

Sources & evidence

ORD record
ord-887d08d5f6c5411bb932b15981ae8026
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

Loading…