Sodium Iodoacetate → [2-(3-Chloro-phenyl)-ethoxy]-acetic acid methyl ester

To a solution of 2-(3-chloro-phenyl)-ethanol (1.96 g, 12.51 mmol) in THF (55 ml) was added n-BuLi (8.8 ml, 1.6 M solution in hexane, 13.77 mmol) at −78° C. Then sodium iodoacetate (2.6 g, 12.51 mmol) was added and the mixture was allowed to warm to ambient temperature and was stirred overnight. The THF was then removed and 1 N HCl was added to the remaining residue to adjust the pH to 1. This mixture was extracted two times with dichloromethane and the combined extracts were dried (Na2SO4) and evaporated. The remaining red liquid was dissolved in MeOH (60 ml) and thionylchloride (1.56 ml, 21.5 mmol) was added dropwise at −15° C. The reaction mixture was then stirred for 1.5 h at ambient temperature. Then water was added and the mixture was extracted three times with ether. The combined extracts were washed with brine, dried (Na2SO4) and evaporated. The remaining residue was then purified by column chromatography (silica gel, heptane/ethyl acetate 95:5 to 88:12) to give the title compound (2.161 g, 9.45 mmol; 76%) as orange liquid. MS: m/e=229.2 [M+H+].

1. customThe THF was then removed
2. addition1 N HCl was added to the remaining residue
3. extractionThis mixture was extracted two times with dichloromethane
4. dry with materialthe combined extracts were dried (Na2SO4)
5. customevaporated
6. dissolutionThe remaining red liquid was dissolved in MeOH (60 ml)
7. stirringThe reaction mixture was then stirred for 1.5 h at ambient temperature
8. extractionthe mixture was extracted three times with ether
9. washThe combined extracts were washed with brine
10. dry with materialdried (Na2SO4)
11. customevaporated
12. customThe remaining residue was then purified by column chromatography (silica gel, heptane/ethyl acetate 95:5 to 88:12)

ORD record

ord-50c02981914a48769e8710de86a59d4b

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928106B2