Acetic Acid → HCID 59638321, compound

In a 250 mL three neck bottle magnesium turnings (5.2 g, 214 mmol, 2.35 eq.) are mixed with tetrahydrofuran (10 ml). Whilst stirring 5-(brommethyl)-bicyclo[2.2.1]hept-2-ene (17 g, 90.8 mmol, 1.03 eq.) that is dissolved in tetrahydrofuran (25 ml) is added dropwise. After stirring for one hour the excess of magnesium turnings is filtered off. The solution is added dropwise to a mixture of 1,3-dibromopropan (17.9 g, 88 mmol, 1 eq.), Li2CuCl4 (0.1 M in THF) (9 ml, 0.9 mmol, 0.01 eq.) and tetrahydrofuran (35 ml). After complete addition of the Grignard reagent, the black solution is stirred for one hour more. The reaction mixture is hydrolyzed with acetic acid (20%). Diethylether (40 ml) is added and the organic phase is washed with saturated sodium hydrogencarbonate solution (30 ml) and distilled water (30 ml). The organic layer is dried over magnesium sulfate and the solvent evaporated in vacuo at room temperature. The product is distilled at 20 mbar and 140° C. A colourless oil is obtained (Yield: 10.31 g, 45 mmol, 51%).

1. additionis added dropwise
2. filtrationis filtered off
3. washthe organic phase is washed with saturated sodium hydrogencarbonate solution (30 ml)
4. distillationdistilled water (30 ml)
5. dry with materialThe organic layer is dried over magnesium sulfate
6. customthe solvent evaporated in vacuo at room temperature
7. distillationThe product is distilled at 20 mbar and 140° C
8. customA colourless oil is obtained (Yield: 10.31 g, 45 mmol, 51%)

ORD record

ord-84b597a9bc2f4f7791f7f7567c405f4d

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09120900B2