Dimethyl Sulfoxide → 2,3-Dihydro-1-benzofuran-7-carbaldehyde

HRID 342089Notes

Reaction equation

HRID 342089 reaction equation
[O:1]1[C:5]2[C:6]([CH2:10][OH:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.CS(C)=O.C(Cl)(=O)C(Cl)=O>C(N(CC)CC)C>[O:1]1[C:5]2[C:6]([CH:10]=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 2795020(2,3-Dihydro-1-benzofuran-7-yl)methanol

Product 1

HCID 27950182,3-Dihydro-1-benzofuran-7-carbaldehydeYield 95.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 2,3-dihydro-benzofuran-7-methanol (8.13 g, 54.5 mmol) was oxidized using DMSO, oxalyl chloride, and triethyl amine similar to the above procedures to give the product as an oil (7.7 g, 95%).

Sources & evidence

ORD record
ord-a852a7612a1547eda322c0ef871cb06e
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

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