Dimethyl Sulfoxide → HCID 86758781, compound

To a solution of oxalyl chloride (0.21 mL, 2.4 mmol) in anhydrous dichloromethane (30 mL) at −78° C. under nitrogen atmosphere, dimethylsulfoxide (0.36 mL, 5.0 mmol) was added and stirred for 30 minutes. To this mixture, a solution of ethyl (1SR,2SR,3RS)-2-hydroxymethyl-3-ethylcyclopropane carboxylate (350 mg, 2.0 mmol) in anhydrous dichloromethane (20 mL) was added and reaction stirred at the same temperature for 45 minutes. Then, triethylamine (1.4 mL, 10.0 mmol) was added and the mixture was allowed to react at room temperature. After 30 minutes, the reaction was quenched with water (30 mL), the layers were separated and the aqueous one was extracted with dichloromethane (2×50 mL). The combined organic layers were dried over sodium anhydride, filtered and evaporated to dryness. The resulting residue was purified by column chromatography using ethyl acetate and hexane 1:4 as eluent to afford 310 mg (90% yield) of ethyl (1SR,2SR,3RS)-2-formyl-3-ethylcyclopropane carboxylate.

1. customreaction
2. stirringstirred at the same temperature for 45 minutes
3. customto react at room temperature
4. waitAfter 30 minutes
5. customthe reaction was quenched with water (30 mL)
6. customthe layers were separated
7. extractionthe aqueous one was extracted with dichloromethane (2×50 mL)
8. dry with materialThe combined organic layers were dried over sodium anhydride
9. filtrationfiltered
10. customevaporated to dryness
11. customThe resulting residue was purified by column chromatography

ORD record

ord-129306cfcf034d6386fbbd88eff092fb

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06504052B1