1,4-Dioxane → 5,6-Dihydrofuro[2,3-c]pyridazine-3-carbaldehyde

HRID 15180Notes

Reaction equation

HRID 15180 reaction equation
[CH:1]([C:3]1[N:8]=[N:7][C:6]2[O:9][CH2:10][CH2:11][C:5]=2[CH:4]=1)=C.I([O-])(=O)(=O)=[O:13].[Na+].O1CCOCC1>O.[Os](=O)(=O)(=O)=O>[N:7]1[C:6]2[O:9][CH2:10][CH2:11][C:5]=2[CH:4]=[C:3]([CH:1]=[O:13])[N:8]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 23667635Sodium periodateHCID 675273573-Ethenyl-5,6-dihydrofuro[2,3-c]pyridazine

Product 1

HCID 824175235,6-Dihydrofuro[2,3-c]pyridazine-3-carbaldehydeYield 20.7%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 3-ethenyl-5,6-dihydrofuro[2,3-c]pyridazine (110 mg, 0.74 mmol), 4% osmium tetroxide in water (0.66 ml), sodium periodate (367 mg), 1,4-dioxane (6.6 ml) and water (1.3 ml) was stirred for 3 hours. The mixture was evaporated and the residue treated with chloroform and added to the top of a column. Elution with ethyl acetate afforded the product (23 mg).

Workup

  1. customThe mixture was evaporated
  2. additionthe residue treated with chloroform
  3. additionadded to the top of a column
  4. washElution with ethyl acetate

Sources & evidence

ORD record
ord-115a06c9682f4b8988d8d9d6bfebb58a
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Reaction notes

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