p-Toluenesulfonic acid → HCID 21898047, compound

Temperature

-78 °C

A solution of thiophene (0.60 mL, 7.5 mmol) in THF (15 mL) was cooled to −78° C., BuLi solution (2.5 M in hexanes, 3.0 mL, 7.5 mmol) was added dropwise, after 1 h at −78° C., a solution of 1-(4-hydroxy-phenyl)-ethanone (1.0 g, 7.34 mmol) was added. The slurry mixture was stirred at −78° C. for 2 h, then slowly warmed to rt. The reaction was quenched with saturated aqueous NH4Cl, extracted with ethyl acetate, the extract was washed with brine, dried over MgSO4 and concentrated to give yellow oil residue. To the above oil residue was added benzene (10 mL) and catalytic amount of TsOH. The mixture was heated with Dean-Stark trap for 15 min, then concentrated 4-(1-Thiophen-2-yl-vinyl)-phenol (170 mg, 11.5%) was obtained after flash column chromatography (20%–40% ethyl acetate-hexanes). MS Found: (M+H)+=203.

1. temperatureslowly warmed to rt
2. customThe reaction was quenched with saturated aqueous NH4Cl
3. extractionextracted with ethyl acetate
4. washthe extract was washed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. customto give yellow oil residue
8. temperatureThe mixture was heated with Dean-Stark trap for 15 min

ORD record

ord-c1ea259963194937a9dd73b011f301cc

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07132432B2