Allyl bromide → Ethyl 2-allylindane-2-carboxylate

To a solution of ethyl indane-2-carboxylate [Schaaf et al., J. Med. Chem. 1983, 26, 328-334] (6.87 g, 36.1 mmol) in THF (100 mL) at −78° C. was added sodium his(trimethylsilyl)amide (1.0 M in THF, 39.7 mL, 39.7 mmol) drop wise over 20 min. The resulting yellow solution was stirred for 1 h, and then allyl bromide (3.75 mL, 43.3 mmol) was added over 5 minutes. Stirring was continued for 1.5 h at −78° C., and then the reaction was quenched by the addition of saturated NH4Cl (50 mL) and warmed to ambient temperature. The reaction mixture was partitioned between saturated NH4Cl (100 mL) and EtOAc (100 mL). The aqueous phase was further extracted with EtOAc (2×50 mL), and the combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc-100:0 to 75:25, to give the title compound. MS: m/z=231 (M+1).

1. stirringStirring
2. waitwas continued for 1.5 h at −78° C.
3. customthe reaction was quenched by the addition of saturated NH4Cl (50 mL)
4. customThe reaction mixture was partitioned between saturated NH4Cl (100 mL) and EtOAc (100 mL)
5. extractionThe aqueous phase was further extracted with EtOAc (2×50 mL)
6. dry with materialthe combined organic layers were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude product was purified by silica gel chromatography
10. washeluting with a gradient of hexane

ORD record

ord-3a9568eb70d54c5086d648e34cad33a3

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003792B2