Dimethyl Sulfone → Methanesulfonylacetic acid methyl ester

To a suspension of dimethyl sulfone (5.43 g) in tetrahydrofuran (10 mL) was addded 1.59 M n-butyl lithium (36.3 mL) in a dryice-acetone bath under a nitrogen atmosphere. After stirring for 0.5 hour, a solution of methyl methoxyacetate (2.00 g) in tetrahydrofuran (5 mL) was added. The resulting mixture was stirred for 2 hours in the bath and allowed to warm to room temperature over 2 hours. The mixture was partitioned between EtOAc and 4 N hydrochloric acid. The reaction was quenched by adding 4 N hydrochloric acid in EtOAc (15 mL). The mixture was partitioned between EtOAc (100 mL) and brine (100 mL). The aqueous layer was washed with EtOAc (100 mL, five times). The organic layer was combined, and the combined extracts were dried over MgSO4, and evaporated. Flash silicagel column chromatography (EtOAc-hexane=50-200 to 300-100) afforded 2-(methylsulfonyl)-1-methoxyethanone as a colorless oil (2.24 g).

1. stirringThe resulting mixture was stirred for 2 hours in the bath
2. customThe mixture was partitioned between EtOAc and 4 N hydrochloric acid
3. customThe reaction was quenched
4. additionby adding 4 N hydrochloric acid in EtOAc (15 mL)
5. customThe mixture was partitioned between EtOAc (100 mL) and brine (100 mL)
6. washThe aqueous layer was washed with EtOAc (100 mL, five times)
7. dry with materialthe combined extracts were dried over MgSO4
8. customevaporated

ORD record

ord-889ff1b3676848589e8fadc59cb58891

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07153854B2