Dimethyl Sulfoxide → 5-Methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carbaldehyde

Temperature

50 °C

DMSO (1.7 ml, 24 mmol) in 5 ml CH2Cl2 was cooled to −50–60° C. Oxalyl chloride (1 ml, 11 mmol) in 20 ml DCM was then added within 5 minutes at 50° C. The mixture was kept at −50° C. for 5 minutes and then 1.67 gram (9 mmol) of (5-Methyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-2-yl)-methanol in 20 ml DCM was added at 50° C. and the mixture was stirred for another 15 minutes at 50° C. Triethylamine (7 ml) was then added at −50° C. and after 5 minutes the bath was removed and the mixture is naturally warmed up to 23° C. It was washed with 100 ml water and extracted with 100 ml ethyl acetate. The combined organic layers were dried over magnesium sulfate. Filter. Concentrate and flash column chromatograph using 0–15% methanol in ethyl acetate yielded 736 mg (45% yield) product.

1. customwas removed
2. temperaturethe mixture is naturally warmed up to 23° C
3. washIt was washed with 100 ml water
4. extractionextracted with 100 ml ethyl acetate
5. dry with materialThe combined organic layers were dried over magnesium sulfate
6. filtrationFilter
7. concentrationConcentrate

ORD record

ord-47c39d0311c4406ea520ad0b1472fdac

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07112582B2