Water → HCID 66609412, compound

Temperature

-78 °C

A solution of thiophene (5.71 g, 67.9 mmol) in dry THF (60 mL) was cooled to −78° C. under nitrogen. A solution of n-BuLi (26.0 mL, 2.5 M, 65.0 mmol) was then added dropwise. After addition, the reaction mixture was stirred at −78° C. for additional 1 hour, before a solution of 2-butyloctyliodide (16.0 g, 54.0 mmol) in dry THF (30 mL) was added slowly. This mixture was stirred at −78° C. for 1 hour, and then allowed to warm to room temperature slowly and stirred at room temperature for 38 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with ether. The organic layer was washed with water and brine, dried over MgSO4, and concentrated on a rotary evaporator. The residue was subjected to column chromatography on silica gel with hexane as the eluent, leading to a colorless oil as the product (4.95 g, 36.3%).

1. additionAfter addition
2. additionwas added slowly
3. temperatureto warm to room temperature slowly
4. stirringstirred at room temperature for 38 hours
5. extractionthe resulting mixture was extracted with ether
6. washThe organic layer was washed with water and brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated on a rotary evaporator

ORD record

ord-96cb65cf22c74a3c8cc4aec9fdaaf072

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598575B2