Triethylamine → 1-Methylsulfonyloxy-5-phenylpentane

A stirred solution of 25.0 grams (0.152 mole) of 5-phenylpentanol and 23.3 mL (0.167 mole) of triethylamine in 250 mL of methylene chloride was cooled to 0° C., and a solution of 13.0 mL (0.167 mole) of methanesulfonyl chloride in 50 mL of methylene chloride was added dropwise at a rate to maintain the reaction mixture temperature at 0° C. to 5° C. The complete addition required about 45 minutes. Upon completion of addition, the reaction mixture was allowed to warm to ambient temperature. After this time the reaction mixture was washed with two 200 mL portions of an aqueous 5% sodium bicarbonate solution and then with 200 mL of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 36.8 grams of 1-methylsulfonyloxy-5-phenylpentane. The NMR spectrum was consistent with the proposed structure.

1. temperatureto maintain the reaction mixture temperature at 0° C. to 5° C
2. additionThe complete addition required about 45 minutes
3. additionUpon completion of addition
4. washAfter this time the reaction mixture was washed with two 200 mL portions of an aqueous 5% sodium bicarbonate solution
5. dry with materialThe organic layer was dried with magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-33db3db7920e411ea68960a7acd96006

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05587379