Hexane → HCID 101372458, compound

An oven dried 500 mL round bottom flask with nitrogen atmosphere was charged with hexane (100 mL), tetrahydrofuran (20 mL), and trimethylsilylacetylene (4.8 g, 48.9 mmol) and cooled with an ice bath. N-butyllithium (2.5 M in hexane, 19.4 mL) was added dropwise and the reaction mixture was allowed to warm to room temperature. The reaction product (20.0 g) from the previously described step, “Synthesis of 3-(N-methylnonafluorobutanesulfonamido)propyl) diisopropylsilyl chloride,” was slowly added and the contents allowed to stir for sixteen hours. Water was added slowly (100 mL) and the mixture was stirred vigorously. The organic layer was separated, and the water layer extracted with 100 mL of hexane. The organic layers were combined and concentrated under reduced pressure to a brown oil. The oil was purified using chromatography on silica gel with hexane as an eluant, resulting in 23.9 g of the trimethylsilyl-protected acetylene as a clear oil. The oil (23.9 g, 42.2 mmol) was charged to an oven dried 500 mL round bottom flask. Methanol (50 mL), tetrahydrofuran (50 mL), and 5% aqueous NaOH (1 mL) were added to the flask and then stirred for one hour. Water (100 mL) was then added, and stirred vigorously. The organic layer was separated, and the aqueous layer was extracted two times with hexane (2×100 mL). The organic layers were combined and concentrated under reduced pressure to yield 3-(N-methylnonafluorobutanesulfonamido)propyl)diisopropylsilyl acetylene as a clear oil (11.2 g, 54%).

1. customAn oven dried 500 mL round bottom flask with nitrogen atmosphere
2. temperaturecooled with an ice bath
3. additionwas slowly added
4. stirringthe mixture was stirred vigorously
5. customThe organic layer was separated
6. extractionthe water layer extracted with 100 mL of hexane
7. concentrationconcentrated under reduced pressure to a brown oil
8. customThe oil was purified
9. customresulting in 23.9 g of the trimethylsilyl-protected acetylene as a clear oil
10. customdried 500 mL round bottom flask
11. additionMethanol (50 mL), tetrahydrofuran (50 mL), and 5% aqueous NaOH (1 mL) were added to the flask
12. stirringstirred for one hour
13. additionWater (100 mL) was then added
14. stirringstirred vigorously
15. customThe organic layer was separated
16. extractionthe aqueous layer was extracted two times with hexane (2×100 mL)
17. concentrationconcentrated under reduced pressure

ORD record

ord-aa3f41655ccb4ee8acc9aece87a4667e

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08920679B2