Methyl morpholine oxide → HCID 86669880, compound

HRID 1506347Notes

Reaction equation

HRID 1506347 reaction equation
[CH:1]([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:13]2[O:17][N:16]=[C:15]3[C:18]4[C:23]([CH2:24][CH2:25][C:14]=23)=[CH:22][C:21]([CH:26]=C)=[CH:20][CH:19]=4)=[CH:9][C:6]=1[C:7]#[N:8])([CH3:3])[CH3:2].C[N+]1([O-])CC[O:32]CC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[CH:26]([C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[C:15]1=[N:16][O:17][C:13]([C:10]3[CH:11]=[CH:12][C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[C:6]([CH:9]=3)[C:7]#[N:8])=[C:14]1[CH2:25][CH2:24]2)=[O:32]

Participants

7

Reactant 3

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 67170307HCID 67170307, compound

Product 1

HCID 86669880HCID 86669880, compoundYield 71.3%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-isopropoxy-5-(7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazol-3-yl)benzonitrile (Preparation 15C, 0.088 g, 0.247 mmol) in THF (1.5 mL) was added N-methylmorpholine-N-oxide (50% in water) (0.17 mL, 0.370 mmol) followed by osmium tetroxide (0.039 mL, 4.94 μmol) at room temperature. The contents were stirred at room temperature for 3.5 h. Sodium periodate (0.106 g, 0.494 mmol) dissolved in 0.5 mL of water was added over a period of 2 min. at room temperature and the contents were stirred at room temperature for 1 h. The reaction mixture was concentrated and partitioned between ethyl acetate (15 mL) and water (10 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated to yield 5-(7-formyl-4,5-dihydronaphtho[1,2-c]isoxazol-3-yl)-2-isopropoxybenzonitrile (0.090 g, 0.176 mmol, 71% yield) as an orange-yellow solid. LC/MS M+1=359.1.

Workup

  1. additionwas added over a period of 2 min. at room temperature
  2. stirringthe contents were stirred at room temperature for 1 h
  3. concentrationThe reaction mixture was concentrated
  4. custompartitioned between ethyl acetate (15 mL) and water (10 mL)
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6b68926e36c7481e8d6bb6e6e30e4888
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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