Dimethyl Sulfoxide → 3,4-Dihydro-2H-1-benzopyran-5-carboxaldehyde

HRID 1107553Notes

Reaction equation

HRID 1107553 reaction equation
[CH2:1]1[CH2:10][O:9][C:8]2[C:3](=[C:4]([CH2:11][OH:12])[CH:5]=[CH:6][CH:7]=2)[CH2:2]1.CS(C)=O.C(Cl)(=O)C(Cl)=O>C(N(CC)CC)C>[CH2:1]1[CH2:10][O:9][C:8]2[C:3](=[C:4]([CH:11]=[O:12])[CH:5]=[CH:6][CH:7]=2)[CH2:2]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 187874603,4-Dihydro-2H-1-benzopyran-5-methanol

Product 1

HCID 187874813,4-Dihydro-2H-1-benzopyran-5-carboxaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

(2H-3,4-Dihydrobenzopyran-5-yl)methanol was oxidized using DMSO, oxalyl chloride, and triethyl amine similar to the above procedures to give the product as a clear oil (100%).

Sources & evidence

ORD record
ord-46d1d4c75ecb4069a24d5aea8eba1e13
Source dataset
uspto-grants-2000_05
Patent number
US06060506

Reaction notes

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