Diethyl Ether → HCID 9818417, compound

In a 10 mL oven-dried flask charged with Mg turnings (0.12 g, 4.9 mmol) which was activated under vacuum by the use of a heat-gun. Under inert atmosphere was added a suspension of 1-bromo-2-ethylbenzene (0.66 g, 3.6 mmol) in Et2O (2 mL) and the reaction mixture was allowed to reflux for 2 hours. A suspension of compound 4 (0.50 g, 2.4 mmol) in CH2Cl2 (2 mL) was added via a syringe and the reaction mixture was stirred at rt overnight. The reaction mixture was quenched by addition of H2SO4 (14 mL, 2 M) and stirred at rt for 2 hours followed by addition of NaOH (20 mL, 2 M). Addition of THF (20 mL) was followed by extraction with ethyl acetate (3×50 mL) and the combined organic phases are washed with brine (10 mL) and NaOH (10 mL, 2 M), and the organic phases were dried (MgSO4) and evaporated to dryness to produce 0.75 g of crude 21. The crude product was subjected to CC [eluent: CH2Cl2: MeOH (99:1)] to give pure 21 (0.68 g, 90%); LC-MS [M+H]+ 315 (cald. 315.5).

1. customIn a 10 mL oven-dried flask
2. additionUnder inert atmosphere was added
3. temperatureto reflux for 2 hours
4. additionwas added via a syringe
5. customThe reaction mixture was quenched by addition of H2SO4 (14 mL, 2 M)
6. stirringstirred at rt for 2 hours
7. additionfollowed by addition of NaOH (20 mL, 2 M)
8. additionAddition of THF (20 mL)
9. extractionwas followed by extraction with ethyl acetate (3×50 mL)
10. washthe combined organic phases are washed with brine (10 mL) and NaOH (10 mL, 2 M)
11. dry with materialthe organic phases were dried (MgSO4)
12. customevaporated to dryness
13. customto produce 0.75 g of crude 21

ORD record

ord-cf5ce3de2f3e4ff2b336c542db71f38e

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07485651B2