Magnesium bromide diethyl etherate → Phytanyl Bromide

To a suspension of magnesium bromide diethyl etherate (25.9 g, 100.3 mmol) in anhydrous diethyl ether (250 mL) under nitrogen at room temperature was added a solution of phytanyl mesylate (18.9 g, 50.2 mmol) in anhydrous diethyl ether (200 mL) dropwise over 15 minutes. The resulting slurry was stirred for 72 hours at room temperature. Upon completion, the reaction mixture was cooled to 0° C. and ice cold water was added dropwise until all solid dissolved and bubbling stopped. Diethyl ether (300 mL) was added, and the organic and aqueous layers separated. The aqueous layer was back-extracted with diethyl ether (200 mL). The combined diethyl ether extracts were dried on MgSO4, filtered, and concentrated. The resulting oil was purified by column chromatography (column 10″L×2″W; eluted with 100% hexanes) to afford the product as a pale yellow oil (16.3 g, 90%).

1. temperatureUpon completion, the reaction mixture was cooled to 0° C.
2. additionice cold water was added dropwise until all solid
3. dissolutiondissolved
4. custombubbling
5. additionDiethyl ether (300 mL) was added
6. customthe organic and aqueous layers separated
7. extractionThe aqueous layer was back-extracted with diethyl ether (200 mL)
8. dry with materialThe combined diethyl ether extracts were dried on MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe resulting oil was purified by column chromatography (column 10″L×2″W; eluted with 100% hexanes)

ORD record

ord-c79d6af0c51b458096e518832148653f

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08865675B2