HCID 19603510, compound → HCID 19603443, compound

HRID 1604578Notes

Reaction equation

HRID 1604578 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[CH:20]=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:23].[Na+]>O1CCOCC1.O.C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[C:16]([CH3:19])[CH:15]=[C:14]2[CH:20]=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 19603510HCID 19603510, compoundHCID 23667635Sodium periodate

Product 1

HCID 19603443HCID 19603443, compoundYield 61.1%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a stirred solution of 8-benzyloxy-2-methyl-4-vinylquinoline (200 mg) in 1,4-dioxane-water (3:1, V/V, 1 ml) was added catalytic amount of osmium tetroxide in tert-butanol in an ice bath. Sodium periodate (342 mg) was added to the reaction mixture portionwise and the resulting suspension was vigorously stirred overnight at ambient temperature. The mixture was extracted with ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo to give a brown oil. This was purified by a silica gel column eluting with ethyl acetate-n-hexane (1:3, V/V) to give 8-benzyloxy-4-formyl-2-methylquinoline as a yellow solid (123 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a brown oil
  6. customThis was purified by a silica gel column
  7. washeluting with ethyl acetate-n-hexane (1:3, V/V)

Sources & evidence

ORD record
ord-4cca8e57d1464e53a759f8383509904e
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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