1-Propene, 3-methoxy- → Ethyl 3-(3-methoxypropyl)benzoate

Temperature

0 °C

To a THF solution (0.1 M) of allyl methyl ether (1.4 eq.) was added, at 0° C., 9-borabicyclo[3.3.1]nonane (2.4 eq.) over a period of 30 min. The solution was stirred at 0° C. for 1 h and then warmed slowly to RT over 16 h. To the resulting clear solution was then added sodium methoxide (2.4 eq.), Cl2Pd(dppf)-dichloromethane complex (5% loading) and ethyl 3-bromobenzoate (1 eq.). The now brown suspension was heated to reflux for 16 h. The reaction mixture was cooled to RT, quenched with sat. aq. NH4Cl and extracted with ether. The combined organic extracts were washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded a brown oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→4:1 (v/v) Hex:EtOAc) afforded the title compound as a light yellow oil.

1. temperaturewarmed slowly to RT over 16 h
2. temperatureThe now brown suspension was heated
3. temperatureto reflux for 16 h
4. temperatureThe reaction mixture was cooled to RT
5. customquenched with sat. aq. NH4Cl
6. extractionextracted with ether
7. washThe combined organic extracts were washed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customConcentration of the filtrate in vacuo afforded a brown oil
11. customPurification of the crude product
12. customthus obtained by way of flash chromatography (SiO2, Hex→4:1 (v/v) Hex:EtOAc)

ORD record

ord-4adac288e2444c31ab9ac38dd0ab4339

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2