Methyl morpholine oxide → HCID 86669884, compound

HRID 1506360Notes

Reaction equation

HRID 1506360 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]3[CH2:15][CH2:16][C:17]4[C:22]([C:13]=3[O:12][N:11]=2)=[CH:21][CH:20]=[C:19]([CH:23]=C)[CH:18]=4)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C[N+]1([O-])CC[O:29]CC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[CH2:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:14]3[CH2:15][CH2:16][C:17]4[C:22]([C:13]=3[O:12][N:11]=2)=[CH:21][CH:20]=[C:19]([CH:23]=[O:29])[CH:18]=4)=[CH:8][CH:9]=1)[CH2:2][CH3:3]

Participants

7

Reactant 3

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 67171363HCID 67171363, compound

Product 1

HCID 86669884HCID 86669884, compoundYield 92.2%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3-(4-propylphenyl)-7-vinyl-4,5-dihydronaphtho[2,1-d]isoxazole (Preparation 20D, 0.205 g, 0.650 mmol) in THF (2 mL) were added sequentially N-methylmorpholine-N-oxide (0.3 mL, 0.650 mmol) and osmium tetroxide (0.102 mL, 0.013 mmol) at room temperature. The contents were stirred at room temperature for 85 h. Next, sodium periodate (0.209 g, 0.975 mmol) dissolved in 1.5 mL of water was added at room temperature and the reaction mixture was stirred at room temperature for 1 h. The reaction mixture was partitioned between ethyl acetate (20 mL) and brine (20 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated to yield 3-(4-propylphenyl)-4,5-dihydronaphtho[2,1-d]isoxazole-7-carbaldehyde (0.19 g, 0.599 mmol, 92% yield) as a tan solid. LCMS M+1=318.2.

Workup

  1. additionwas added at room temperature
  2. stirringthe reaction mixture was stirred at room temperature for 1 h
  3. customThe reaction mixture was partitioned between ethyl acetate (20 mL) and brine (20 mL)
  4. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6caeb4b4b529419a9c831e5e98059179
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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