Dimethyl Sulfoxide → 1-Benzofuran-7-carbaldehyde

HRID 342086Notes

Reaction equation

HRID 342086 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[O:11]1[C:15]2[C:16]([CH2:20][OH:21])=[CH:17][CH:18]=[CH:19][C:14]=2[CH:13]=[CH:12]1.C(N(CC)CC)C>C(Cl)Cl>[O:11]1[C:15]2[C:16]([CH:20]=[O:21])=[CH:17][CH:18]=[CH:19][C:14]=2[CH:13]=[CH:12]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18787422Benzofuran-7-ylmethanol

Product 1

HCID 111264061-Benzofuran-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

DMSO (2.87 ml, 40 mmol) was added slowly to a -78° C. solution of oxalyl chloride in methylene chloride (20 ml of 2M, 40 mmol). To this solution was added slowly a solution of benzofuran-7-methanol (4.03 g, 27 mmol) in methylene chloride, and the mixture was stirred 30 min at -78° C. Triethyl amine (30 ml) was added slowly to the reaction mixture, which was then allowed to warm to room temperature. The mixture was diluted with methylene chloride and washed with water and then with brine. The organic layer was concentrated in vacuo to an oil (3.16 g, 80%).

Workup

  1. temperatureto warm to room temperature
  2. washwashed with water
  3. concentrationThe organic layer was concentrated in vacuo to an oil (3.16 g, 80%)

Sources & evidence

ORD record
ord-bc10ad6f1cb84183912e10aad1cd7d58
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

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