1,4-Dioxane → HCID 82374203, compound

HRID 273342Notes

Reaction equation

HRID 273342 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH3:11])=[CH:9][S:8][C:7]=2[CH:12]=1.[O:13]1CCOCC1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH:11]=[O:13])=[CH:9][S:8][C:7]=2[CH:12]=1

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 18448608HCID 18448608, compound

Product 1

HCID 82374203HCID 82374203, compoundYield 80%

Procedure

A mixture of 6-methoxy-3-methylbenzo[b]thiophene (2.753 g, 15.5 mmol) and SeO2 (2.06 g, 18.55 mmol) in 1,4-dioxane (30 mL) was refluxed for 2 days and then filtered. The filtrate was concentrated in vacuo, and the residue was purified on a silica gel column eluting with EtOAc/hexane (1:10) to give 6-methoxybenzo[b]thiophene-3-carbaldehyde (2.3 g, 80%).

Workup

  1. temperaturewas refluxed for 2 days
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified on a silica gel column
  5. washeluting with EtOAc/hexane (1:10)

Sources & evidence

ORD record
ord-8b3ce34a482e4281af76a91eec4c6e36
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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