3-(2-Bromo-thiophen-3-yl)-propionic acid ethyl ester → 3-(2-Bromothiophen-3-yl)propan-1-ol

Temperature

0 °C

A −78° C. solution of the ester of Example 23(e) (3.896 g, 14.8 mmol) in dry toluene (30 mL, Aldrich) was treated with Dibal (21 mL, 31.5 mmol, 1.5 M/toluene, Aldrich). After 1 h, the mixture was allowed to warm to 0° C. and after a further 1 h, the reaction was quenched by addition of 6 M HCl (30 mL). The mixture was stirred for 15 min. and then was extracted with ether (50 mL). The ether solution was washed with 1 M HCl (2×30 mL) and brine (30 mL) and then was dried (MgSO4), filtered, evaporated and purified by flash chromatography (20% ethyl acetate/hexanes→30%) to give 3-(2-Bromo-thiophen-3-yl)-propan-1-ol (3.224 g, 14.6 mmol, 99%).

1. customthe reaction was quenched by addition of 6 M HCl (30 mL)
2. extractionwas extracted with ether (50 mL)
3. washThe ether solution was washed with 1 M HCl (2×30 mL) and brine (30 mL)
4. dry with materialwas dried (MgSO4)
5. filtrationfiltered
6. customevaporated
7. custompurified by flash chromatography (20% ethyl acetate/hexanes→30%)

ORD record

ord-57563f83cc11400d89112b2e0d7ecf5a

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06511999B2