Furan → HCID 66609564, compound

Temperature

-78 °C

A solution of furan (8.16 g, 0.13 mol) in dry THF (100 mL) was cooled to −78° C. under nitrogen. A solution of n-BuLi (28.0 mL, 2.5 M, 70.0 mmol) was then added dropwise. After addition, the reaction mixture was stirred at −78° C. for additional 1 hour, before a solution of (S)-2-methylbutyliodide (10.0 g, 50.5 mmol) in dry THF (20 mL) was added slowly. This mixture was stirred at −78° C. for 2 hours, and then allowed to warm to room temperature slowly and stirred at room temperature overnight. The reaction was quenched by water (20 mL) and the mixture was poured into water (200 mL), and the resulting mixture was extracted with ether (300 mL). The organic layer was washed with water and brine, dried over Na2SO4, and concentrated on a rotary evaporator. The residue was subjected to column chromatography on silica gel with hexane as eluent, leading to a colorless oil as the product. (6.18 g, 88.5%).

1. additionAfter addition
2. additionwas added slowly
3. temperatureto warm to room temperature slowly
4. stirringstirred at room temperature overnight
5. customThe reaction was quenched by water (20 mL)
6. additionthe mixture was poured into water (200 mL)
7. extractionthe resulting mixture was extracted with ether (300 mL)
8. washThe organic layer was washed with water and brine
9. dry with materialdried over Na2SO4
10. concentrationconcentrated on a rotary evaporator

ORD record

ord-4e17a39b382341fea5240a0de20f01b7

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598575B2