Triethylamine → HCID 59610029, compound

(4-Mercapto-phenyl)-acetic acid methyl ester (1.8 g, 9.89 mmol) was dissolved in DMF (20 ml) at 0° C. Triethylamine (1.5 g, 14.83 mmol) was added and stirred for 15 minutes followed by addition of 4-iodo-tetrahydropyan (3.14 g, 14.83 mmol). The reaction mixture was stirred overnight at room temperature. Solvent was removed under reduced pressure, the resulting residue was taken into water and extracted with ethyl acetate (50 ml×2) washed with water and brine (50 ml each) dried over anhydrous sodium sulfate, filtered and concentrated to obtain a crude product which was purified by column chromatography over silica gel using 15% ethyl acetate in hexanes as eluent to provide [4-(Tetrahydro-pyran-4-ylsulfanyl)-phenyl]acetic acid methyl ester (2.1 gm).

1. additionfollowed by addition of 4-iodo-tetrahydropyan (3.14 g, 14.83 mmol)
2. stirringThe reaction mixture was stirred overnight at room temperature
3. customSolvent was removed under reduced pressure
4. extractionextracted with ethyl acetate (50 ml×2)
5. washwashed with water and brine (50 ml each)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customto obtain a crude product which
10. customwas purified by column chromatography over silica gel using 15% ethyl acetate in hexanes as eluent

ORD record

ord-a0d97e51d6c347a181facba8807526cb

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501955B2