Benzyltriphenylphosphonium bromide → HCID 69607320, compound

Temperature

0 °C

Benzyltriphenylphosphonium bromide (1.30 g, 3.01 mmol) was suspended in anhydrous THF (6 mL) and cooled to 0° C. This was treated with n-butyllithium (1.20 mL, 3.01 mmol, 2.5M in hexanes) by slow addition. It was then stirred at 0° C. for 1.5 hr. Next it was treated with a solution of 2-t-butoxycarbonylamino-4-formyl-thiophene-3-carboxylic acid ethyl ester (0.300 g, 1.00 mmol) dissolved in anhydrous THF (6 mL) by slow addition. The reaction was allowed to stir at room temperature for 1 hr. It was then quenched with sat. NH4Cl (12 mL). This was extracted with CH2Cl2 (3×25 mL). The combined extracts were washed with H2O (1×25 mL) and brine (1×25 mL). The extracts were dried (Na2SO4), filtered, and the solvent removed in vacuo. The crude product was purified by flash chromatography (SiO2, 1 EtOAc/3 hexanes) to afford the title compound (0.3432 g, 92%). MS m/e (CI) 374.1 (M+H)+; 1H NMR (300 MHz, CDCl3): δ ppm 1.26 (m, 1H), 1.36 (t, 1H), 1.44 (m, 1H), 1.54 (s, 9H), 4.35 (m, 1H), 6.34 (s, 1H), 6.59 (m, 1H), 6.93 (d, 1H), 6.89 (s, 1H), 7.17 (s, 1H), 7.35 (t, 1H), 7.47 (d, 1H), 7.59 (d, 1H), 10.40 (s, 1H).

1. stirringto stir at room temperature for 1 hr
2. customIt was then quenched with sat. NH4Cl (12 mL)
3. extractionThis was extracted with CH2Cl2 (3×25 mL)
4. washThe combined extracts were washed with H2O (1×25 mL) and brine (1×25 mL)
5. dry with materialThe extracts were dried (Na2SO4)
6. filtrationfiltered
7. customthe solvent removed in vacuo
8. customThe crude product was purified by flash chromatography (SiO2, 1 EtOAc/3 hexanes)

ORD record

ord-68e45b338740465b90c6c3fd0385448f

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119205B2