Ethyl Acetate → 5-(2-Benzyloxy-ethyl)-cyclohex-1-enecarboxylic acid methyl ester

Temperature

55 °C

A solution of 5-(2-benzyloxy-ethyl)-2-hydroxy-cyclohexanecarboxylic acid methyl ester (Intermediate A2) (0.72 g, 2.48 mmol) in pyridine (10 mL) was treated with SOCl2 (0.73 mL, 12.4 mmol) (available from Aldrich) at −20° C. The mixture was allowed to react for 15 m and was then warmed to 55° C. for 16 h. The solvents were removed under vacuum and the residue was diluted in ether at 0° C. The solution was quenched with water, washed with 1M, HCl, 5% NaOH and brine. The organic material was dried over MgSO4 filtered and freed of solvent. The mixture was diluted with benzene and water was removed by azeotropic distillation under vacuum. The residue was dissolved in benzene (15 mL) and DBU (0.76 mL, 5 mmol) was added. The mixture was reacted for 30 m at rt. After work-up and chromatography on SiO2 with 20% EtOAc:Hx, 5-(2-benzyloxy-ethyl)-cyclohex-1-enecarboxylic acid methyl ester (Intermediate A3) was isolated 0.56 g (82%).

1. customto react for 15 m
2. customThe solvents were removed under vacuum
3. additionthe residue was diluted in ether at 0° C
4. customThe solution was quenched with water
5. washwashed with 1M, HCl, 5% NaOH and brine
6. dry with materialThe organic material was dried over MgSO4
7. filtrationfiltered
8. additionThe mixture was diluted with benzene and water
9. customwas removed by azeotropic distillation under vacuum
10. dissolutionThe residue was dissolved in benzene (15 mL)
11. customThe mixture was reacted for 30 m at rt

ORD record

ord-47a3327ebee84ec8b4e9a3ed361841e8

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07390829B2