Triethylamine → Butyl methanesulfonate

Temperature

0 °C

3-(2-hydroxyethoxy)-4-(triphenylmethoxy)-1-butanol (14.0 g, 35.7 mmol) was dissolved in 140 mL of CH2Cl2, was cooled to 0° C. under N2, and triethylamine (10.8 g, 14.9 mL, 0.107 mol. 3.0 eq.) was added. Methanesulfonyl chloride (11.0 g, 7.46 mL, 96.4 mmol, 2.7 eq.) was then added dropwise at <5° C. The resultant reaction mixture was diluted with additional CH2Cl2 (300 mL) and was washed with 200 mL of water and 200 mL of an aqueous saturated solution of ammonium chloride. The aqueous layers were back-extracted with 50 mL of CH2Cl2 and the combined organic layer was washed with 100 mL of brine and was dried (MgSO4) and evaporated in vacuo to give 18.4 g (94%) of 3-(2-[(methylsulfonyl)oxy]ethoxy]-4-triphenylmethoxy)-1-butanol methane sulfonate as a white solid.

1. customThe resultant reaction mixture
2. washwas washed with 200 mL of water and 200 mL of an aqueous saturated solution of ammonium chloride
3. extractionThe aqueous layers were back-extracted with 50 mL of CH2Cl2
4. washthe combined organic layer was washed with 100 mL of brine
5. dry with materialwas dried (MgSO4)
6. customevaporated in vacuo

ORD record

ord-c426206e49a34bb38441ee0848d3cdcd

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06015807