Methyl Methanesulfonate → HCID 19940147, compound

Temperature

-78 °C

The lithio derivative of methyl methanesulfonate was prepared at -78° C. under argon by the dropwise addition of 0.56 mL of a 1.60M n-butyllithium (0.891 mmol) to a solution of 72 μL (0.85 mmol) of methyl methanesulfonate in 2 mL of anhydrous tetrahydrofuran. After 45 minutes at -78° C., 3-formyl-2,5-dithienylpyrrole (105 mg, 0.41 mmol) in I mL of tetrahydrofuran was added dropwise over a 5 minute period to the lithio methyl methanesulfonate solution. The reaction mixture was allowed to stir for 30 minutes at -78° C. After the completion of reaction, it was then quenched with a saturated aqueous ammonium chloride solution. The aqueous layer was extracted three times with 50 mL portions of ethyl acetate and the combined organic layers were washed with water (10 mL ×1 ) and brine (10 mL×1). The organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent was removed under reduced pressure. The crude product was purified on 50 g of silica gel. Elution with hexane-ethyl acetate (5:1), gave 64 mg (43%) of title compound.

1. customAfter the completion of reaction, it
2. customwas then quenched with a saturated aqueous ammonium chloride solution
3. extractionThe aqueous layer was extracted three times with 50 mL portions of ethyl acetate
4. washthe combined organic layers were washed with water (10 mL ×1 ) and brine (10 mL×1)
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. customthe solvent was removed under reduced pressure
8. customThe crude product was purified on 50 g of silica gel
9. washElution with hexane-ethyl acetate (5:1)

ORD record

ord-96932ef08d874dd4b401c740ff1e4e02

Source dataset

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE034919