Sodium periodate → 6,7-Dihydro[1,4]oxathiino[2,3-c]pyridazine-3-carbaldehyde

HRID 15153

Reaction equation

HRID 15153 reaction equation
[CH:1]([C:3]1[N:8]=[N:7][C:6]2[O:9][CH2:10][CH2:11][S:12][C:5]=2[CH:4]=1)=C.I([O-])(=O)(=O)=[O:14].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[N:7]1[C:6]2[O:9][CH2:10][CH2:11][S:12][C:5]=2[CH:4]=[C:3]([CH:1]=[O:14])[N:8]=1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 675264963-Ethenyl-6,7-dihydro[1,4]oxathiino[2,3-c]pyridazine

Product 1

HCID 715042546,7-Dihydro[1,4]oxathiino[2,3-c]pyridazine-3-carbaldehydeYield 36%

Reagents, catalysts & solvents 2

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

Procedure

A solution of 3-ethenyl-6,7-dihydro[1,4]oxathiino[2,3-c]pyridazine (320 mg) in 1,4-dioxane/water (20 ml/5 ml) was treated with an aqueous solution of osmium tetroxide (4% w/v, 2 ml) and sodium periodate (1.08 g), initially stirred in an ice-bath, then allowed to warm to room temperature. After 2.5 hours the mixture was evaporated to dryness and dissolved in 1,4-dioxane and chloroform. Silica gel was added and the mixture was evaporated to dryness, added to a silica column (50 g) and chromatographed, eluting with 0-100% ethyl acetate in hexane, to afford a white solid (116 mg, 36%).

Workup

  1. customAfter 2.5 hours the mixture was evaporated to dryness
  2. dissolutiondissolved in 1,4-dioxane
  3. additionSilica gel was added
  4. customthe mixture was evaporated to dryness
  5. additionadded to a silica column (50 g)
  6. customchromatographed
  7. washeluting with 0-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-00096b25ac0a4aa5bdd47d8da325db37
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Linked notes

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