Ethyl Methanesulfonate → Ethyl (diethoxyphosphoryl)methanesulfonate

Temperature

0 °C

To a solution of methanesulfonic acid, ethyl ester (11.00 mL, 0.1068 mol) in THF (200.0 mL, 2.466 mol) at −78° C. was added 2.500 M of n-butyllithium in hexane (50.00 mL) over 15 minutes and the mixture was stirred for 20 minutes. Phosphorochloridic acid, diethyl ester (10.0 mL, 0.0694 mol) was added to the mixture at −78° C. The mixture was stirred for 3.5 hours, allowing to warm to 0° C. The reaction was quenched with 5M ammonium chloride in water (100 mL) and the mixture was concentrated in vacuo to remove THF. The aqueous was extracted with EtOAc (2×150 mL) and the organics were combined and concentrated in vacuo. The product was purified by flash chromatography (0 to 100% EtOAc/Hexanes) to yield the product as an oil (9.07 g, 50%+10.4 g of a mixed fraction).

1. stirringThe mixture was stirred for 3.5 hours
2. customThe reaction was quenched with 5M ammonium chloride in water (100 mL)
3. concentrationthe mixture was concentrated in vacuo
4. customto remove THF
5. extractionThe aqueous was extracted with EtOAc (2×150 mL)
6. concentrationconcentrated in vacuo
7. customThe product was purified by flash chromatography (0 to 100% EtOAc/Hexanes)

ORD record

ord-c3cf5c1b93fe4367a459d70d4197a2f1

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07951810B2