Sodium periodate → HCID 86669893, compound

HRID 1506395Notes

Reaction equation

HRID 1506395 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:14])[F:13])=[C:10]([C:16]3[O:17][C:18]4[C:28]5[C:23](=[CH:24][C:25]([CH:29]=C)=[CH:26][CH:27]=5)[CH2:22][CH2:21][C:19]=4[N:20]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CC[O+:35]([O-])CC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.O=[Os](=O)(=O)=O>[C:1]1([C:7]2[C:11]([C:12]([F:15])([F:13])[F:14])=[C:10]([C:16]3[O:17][C:18]4[C:28]5[C:23](=[CH:24][C:25]([CH:29]=[O:35])=[CH:26][CH:27]=5)[CH2:22][CH2:21][C:19]=4[N:20]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 23667635Sodium periodateHCID 68182011HCID 68182011, compoundHCID 86669894HCID 86669894, compound

Product 1

HCID 86669893HCID 86669893, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent4×HCID 8028TetrahydrofuranSolventHCID 30318Osmium TetroxideSolvent

Procedure

To a stirred solution of 2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-7-vinyl-4,5-dihydronaphtho[2,1-d]oxazole (Preparation 48B, 26.2 mg, 0.064 mmol) in 0.5 mL of THF were added 0.113 mL of 10% N-methyl-morpholine-1-oxide in water and 0.04 mL of 4% OsO4 in water, and 0.2 mL of water. The heterogeneous mixture was stirred at room temperature for 18 hrs. To the homogenous reaction mixture was added 0.14 mL of 10% sodium periodate in water, and the mixture was stirred for 3 hrs. The reaction mixture was extracted with EtOAc, washed with water, brine dried over Na2SO4 and evaporated to give a solid residue which was purified by Combiflash (24 g silica gel) eluting with 1:9 followed by 3:7 EtOAc-hexane to give 2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]oxazole-7-carbaldehyde (20.2 mg, 77% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.69 (1H, s), 7.51-7.61 (2H, m), 7.44 (1H, d, J=7.70 Hz), 7.36 (2H, d, J=7.70 Hz), 7.22-7.30 (3H, m), 2.99-3.05 (2H, m), 2.83 (2H, t, J=8.03 Hz).

Workup

  1. stirringthe mixture was stirred for 3 hrs
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto give a solid residue which
  7. customwas purified by Combiflash (24 g silica gel)
  8. washeluting with 1:9

Sources & evidence

ORD record
ord-adb4403d66954fc195d89d60941bc741
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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