Dimethyl Sulfoxide → 2,3-Dihydro-1-benzofuran-4-carbaldehyde

HRID 849258Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

DMSO (8.10 mL, 114 mmol) was added at -78° C. to a stirred solution of oxalyl chloride in CH2Cl2 (40 mL of a 2M solution). A solution of Part B 2,3-dihydrobenzofuran-4-methanol (8.53 g, 56.9 mmol) in CH2Cl2 (35 mL) was added dropwise, and the solution stirred at -78° C. for 30 min. Triethylamine (33 mL, 228 mmol) was added cautiously to quench the reaction. The resulting suspension was stirred at room temperature for 30 min. and diluted with CH2Cl2 (100 mL). The organic layer was washed three times with water, and twice with brine, and then concentrated in vacuo to give 2,3-dihydrobenzofuran-4-carboxaldehyde as an oil (8.42 g, 100%) that was used without purification.

Workup

customto quench
customthe reaction
stirringThe resulting suspension was stirred at room temperature for 30 min.
washThe organic layer was washed three times with water
concentrationtwice with brine, and then concentrated in vacuo

Sources & evidence

ORD record: ord-08cd37cb4550466eb1595a9739b5c3f8
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011059

Reaction notes

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