Dimethyl Sulfoxide → 1-Benzofuran-7-carbaldehyde

HRID 1107542Notes

Reaction equation

HRID 1107542 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 2 M, 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-ed2c828510ca48738be8970ae1b0a23c
Source dataset
uspto-grants-2000_05
Patent number
US06060506

Reaction notes

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