Triethylamine → HCID 19600067, compound

To a solution of 0.04 ml (0.5 mmol) of oxalyl chloride in 30 ml of dichloromethane, 0.07 ml (1.0 mmol) of dimethyl sulfoxide was added dropwise at -78° C., followed by stirring for 5 minutes. To this solution, a solution of 0.122 g (0.330 mmol) of 4-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-ylsulfonyl)phenylphenylmethanol in 10 ml of dichloromethane and 1 ml of dimethyl sulfoxide was added at -78° C., followed by stirring for 15 minutes. To this mixture, 0.28 ml (2.0 mmol) of triethylamine was added; the mixture was allowed to warm to room temperature. After the reaction mixture was washed with water, the water layer was re-extracted with diethyl ether. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1) to yield the desired product.

1. stirringby stirring for 15 minutes
2. washAfter the reaction mixture was washed with water
3. extractionthe water layer was re-extracted with diethyl ether
4. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
5. distillationthe solvent was distilled off under reduced pressure
6. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

ORD record

ord-2a31341e65e24c83976a86633c6714b7

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998433