4-Toluenesulfonyl chloride → HCID 86607006, compound

A suspension of (R)-α-hydroxy-γ-butyrolactone (3.5 g, 34.3 mmol), tosyl chloride (10.0 g, 52.6 mmol), and K2CO3 (2.23 g, 16.2 mmol) in dry CH2Cl2 (50 mL) was stirred at room temperature overnight. The reaction mixture was filtered, and the filtrate washed with 1M phosphate buffer pH=7 (2×50 mL), 3 M NaCl (aq.) (1×50 mL), dried with Na2SO4, filtered and evaporated to dryness to give the crude product. The crude product was triturated by PE40/60 (50 mL) and stirred for 30 minutes. The precipitate formed was isolated by filtration and washed with PE40/60 to remove trace amounts of tosyl chloride, to give 7.7 g (87%) of enantiopure (R)-α-tosyloxy-γ-butyrolactone. [α]36525=−9.9°.

1. filtrationThe reaction mixture was filtered
2. washthe filtrate washed with 1M phosphate buffer pH=7 (2×50 mL), 3 M NaCl (aq.) (1×50 mL)
3. dry with materialdried with Na2SO4
4. filtrationfiltered
5. customevaporated to dryness
6. customto give the crude product
7. customThe crude product was triturated by PE40/60 (50 mL)
8. stirringstirred for 30 minutes
9. customThe precipitate formed
10. customwas isolated by filtration
11. washwashed with PE40/60
12. customto remove trace amounts of tosyl chloride

ORD record

ord-aca3cf0fa3274bddacf9854709fa83eb

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07632948B2