Methyl morpholine oxide → HCID 86669929, compound

HRID 1506496Notes

Reaction equation

HRID 1506496 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][C:13]=34)=[CH:21][C:20]([CH:24]=C)=[CH:19][CH:18]=5)[C:8]=2[C:26]([F:29])([F:28])[F:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+]1([O-])CC[O:34]CC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]3[O:16][N:15]=[C:14]4[C:17]5[C:22]([CH2:23][C:13]=34)=[CH:21][C:20]([CH:24]=[O:34])=[CH:19][CH:18]=5)[C:8]=2[C:26]([F:27])([F:28])[F:29])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 67170629HCID 67170629, compound

Product 1

HCID 86669929HCID 86669929, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalyst2×HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a clear solution of 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-6-vinyl-4H-indeno[1,2-c]isoxazole (Preparation 87C, 25 mg, 0.063 mmol) in THF (1 mL) were sequentially added NMO (50% in water, 0.016 mL, 0.076 mmol) and osmium tetroxide (4% in water, 0.012 mL, 1.902 μmol) at room temperature. The solution was vigorously stirred at room temperature for 1 hr before more osmium tetroxide (4% in water, 0.02 mL) was added. The mixture was stirred at room temperature overnight. Sodium periodate (17.63 mg, 0.082 mmol) in water (0.1 mL) was added. After the mixture was stirred vigorously at room temperature under nitrogen for 1 hr, water (2 mL) was added. The mixture was concentrated, the solid was filtered, washed with water (1×0.5 mL) and dried to give 3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4H-indeno[1,2-c]isoxazole-6-carbaldehyde as a yellow solid.

Workup

  1. customat room temperature
  2. additionwas added
  3. stirringAfter the mixture was stirred vigorously at room temperature under nitrogen for 1 hr
  4. concentrationThe mixture was concentrated
  5. filtrationthe solid was filtered
  6. washwashed with water (1×0.5 mL)
  7. customdried

Sources & evidence

ORD record
ord-f980b88015444d0b99154002d3875ee4
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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