Water → 3-Methoxypropyl methanesulfonate

Methanesulphonyl chloride (1.75 ml, 22 mmol) was added to a solution of 3-methoxy-1-propanol (1.81 g, 20 mmol) and triethylamine (3.35 ml, 24 mmol) in DCM (40 ml) cooled in an ice bath and the mixture stirred at ambient temperature for 18 hours. DCM (25 ml) and water (50 ml) were added and the phases separated and the aqueous layer was extracted with DCM (25 ml). The extracts were combined, washed with water (50 ml) and brine (50 ml), dried (Chemelut column CE1010) and evaporated to give the title compound 3.25 g (97%) as a pale yellow oil. NMR 2.00 (m, 2H), 3.01 (s, 3H), 3.35 (s, 3H), 3.49 (t, 2H), 4.38 (t, 2H).

1. temperaturecooled in an ice bath
2. customthe phases separated
3. extractionthe aqueous layer was extracted with DCM (25 ml)
4. washwashed with water (50 ml) and brine (50 ml)
5. dry with materialdried (Chemelut column CE1010)
6. customevaporated

ORD record

ord-be49d478818e4e91b976129a57717103

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465728B2