Methyl morpholine oxide → 3-(4-Isopropoxy-2-(trifluoromethyl)phenyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde

HRID 1506349Notes

Reaction equation

HRID 1506349 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]3[C:16]4[C:21]([CH2:22][CH2:23][C:12]=23)=[CH:20][C:19]([CH:24]=C)=[CH:18][CH:17]=4)=[C:7]([C:26]([F:29])([F:28])[F:27])[CH:6]=1)([CH3:3])[CH3:2].C[N+]1([O-])CC[O:34]CC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]3[C:16]4[C:21]([CH2:22][CH2:23][C:12]=23)=[CH:20][C:19]([CH:24]=[O:34])=[CH:18][CH:17]=4)=[C:7]([C:26]([F:28])([F:27])[F:29])[CH:6]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 671709643-(4-Isopropoxy-2-(trifluoromethyl)phenyl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

Product 1

HCID 866698813-(4-Isopropoxy-2-(trifluoromethyl)phenyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehydeYield 98.2%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3-(4-isopropoxy-2-(trifluoromethyl)phenyl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 17B, 0.225 g, 0.563 mmol) in THF (2 mL) was added N-methylmorpholine-N-oxide (50% in water) (0.3 mL, 0.563 mmol) followed by osmium tetroxide (4% in water) (0.088 mL, 0.011 mmol) at room temperature. The contents were stirred at room temperature for 14 h. Sodium periodate (0.181 g, 0.845 mmol) dissolved in 1 mL of water was added at room temperature. The contents were stirred at room temperature for 30 min. The reaction mixture was partitioned between ethyl acetate (10 mL) and brine (5 mL). The dichloromethane layer was dried over sodium sulfate and concentrated to yield 3-(4-isopropoxy-2-(trifluoromethyl)phenyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde (0.222 g, 0.553 mmol, 98% yield). LC/MS M+1=402.1.

Workup

  1. additionwas added at room temperature
  2. stirringThe contents were stirred at room temperature for 30 min
  3. customThe reaction mixture was partitioned between ethyl acetate (10 mL) and brine (5 mL)
  4. dry with materialThe dichloromethane layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9fbb4f3c445b4dd08b098e670d902048
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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