Triethylamine → 7-(Phenyloxy)-1-heptyl methanesulfonate

Temperature

0 °C

A solution of 7-(phenyloxy)-1-heptanol (0.21 g, 1.01 mmol) in anhydrous methylene chloride (20 mL), taken in a 50 mL round bottomed flask was cooled to 0° C. using an ice bath. Methanesulfonyl chloride (0.177 g, 1.55 mmol) was added to this followed by a dropwise addition of triethylamine (0.28 mL, 2.11 mmol). The reaction mixture was then stirred at 0° C. for 1 hour and allowed to attain room temperature in 2hours. It was then quenched with 1N. HCl (10 mL) and diluted with methylene chloride (20 mL). The organic layer was separated and the aqueous layer was extracted with methylene chloride (2×10 mL). The combined organic layer was washed with 1N. HCl (3×10 mL), water (2×10 mL) and brine (2× mL). The organic layer was dried over Na2SO4. Removal of solvent from the dried extract under reduced pressure afforded the product 7-(phenyloxy)-1-heptyl methanesulfonate (0.25 g, 86.5%). The product from the step B was analyzed yielding the following confirmatory data: 1H-NMR (CDCl3) 1.31-1.52 (m, 6H), 1.71-1.84 (m, 4H), 2.98 (s, 3H), 3.94 (t, 2H, J=6.43 Hz), 4.21 (t, 2H, J=6.51 Hz), 6.80-6.94 (m, 3H) and 7.24-7.30 (m, 2H); 13C-NMR (CDCl3) 25.2, 25.7, 28.6, 28.9, 29.0, 37.1, 67.5, 69.9, 114.3, 120.3, 129.2 and 158.9; IR (neat): 1349 cm−1; MS (ES+): 287 (M+1).

1. waitto attain room temperature in 2hours
2. customIt was then quenched with 1N
3. additionHCl (10 mL) and diluted with methylene chloride (20 mL)
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with methylene chloride (2×10 mL)
6. washThe combined organic layer was washed with 1N
7. dry with materialThe organic layer was dried over Na2SO4
8. customRemoval of solvent from the dried
9. extractionextract under reduced pressure

ORD record

ord-9a15a723c02c4bfba6c8e979b3172a91

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06500852B1