Ethyl 4-(mercaptomethyl)-2-methyl-1,3-oxazole-5-carboxylate → 4-(Mercaptomethyl)-2-methyl-1,3-oxazole-5-carbaldehyde

10 mmol of ethyl 4-(mercaptomethyl)-2-methyl-1,3-oxazole-5-carboxylate was dissolved in 100 ml of dried tetrahydrofuran, then 42 ml of the 0.5M SDBBA solution was gradually added with keeping the temperature at −30 to −20° C. After the adding, reaction was carried out for 4 hours at −20° C. Then 20 ml of wafer was added into the reaction system to stop the reaction and then an organic layer was separated. To the remaining water phase, sodium hydrogen carbonate was added until the pH of the water phase reached 8 to 9. The product was extracted and separated into an organic layer using ethyl acetate. This organic layer and the previously obtained organic layer were combined together and dried under sodium sulfate. The solvent was evaporated out and then the product was purified using a column separation with solvents of ethyl acetate and hexane, obtaining 4-(mercaptomethyl)-2-methyl-1,3-oxazole-5-carbaldehyde.

1. addition42 ml of the 0.5M SDBBA solution was gradually added
2. customat −30 to −20° C
3. customAfter the adding, reaction
4. additionThen 20 ml of wafer was added into the reaction system
5. customthe reaction
6. customan organic layer was separated
7. additionTo the remaining water phase, sodium hydrogen carbonate was added until the pH of the water phase
8. extractionThe product was extracted
9. customseparated into an organic layer
10. customdried under sodium sulfate
11. customThe solvent was evaporated out
12. customthe product was purified
13. customa column separation with solvents of ethyl acetate and hexane

ORD record

ord-92888ae2df684810ae2120e3c53724ec

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08779086B2