HCID 56949709, compound → HCID 56949710, compound

The crude isopropenyldiisopropylbromosilane (10.6 g) was treated with 75 mmol of lithium acetylide. The lithium acetylide was formed by saturating an anhydrous THF solution (at −78° C., 200 mL) with acetylene gas that had been passed through a −78° C. cold trap to remove acetone. No further drying of the acetylene gas was undertaken. Once the solution was presumed to be saturated (after 1 hour of flushing the gas through), the solution was treated with n-butyllithium (30 mL, 2.5 M in hexanes, 75 mmol) in a careful dropwise manner so as to maintain the temperature very close to −78° C. After this addition was completed, the isopropenyldiisopropylbromosilane was added as a concentrated solution (˜5 M) in anhydrous THF dropwise to the reaction mixture. The temperature was maintained for an additional 1 hour, then allowed to gradually warm to room temperature. The reaction was quenched by the slow addition of a small amount of saturated ammonium chloride (about 5 mL) and additional water (50 mL). Pentane (100 mL) was added, and the organic layer was separated. The aqueous layer was extracted a second time with pentane (50 mL), and the organic layer separated. The organic layers were washed with water (3×50 mL), dried over MgSO4, filtered, and concentrated on the rotary evaporator. No further purification was performed. Analysis of the liquid product was performed by GC-MS Analysis Method 2. This showed that the area under the peak corresponding to the desired product, (isopropenyldiisopropylsilyl)acetylene with a molecular weight of 180, was 87.34% of the total integrated area indicating a high purity.

1. concentrationby saturating an anhydrous THF solution (at −78° C., 200 mL) with acetylene gas that
2. customhad been passed through a −78° C.
3. customto remove acetone
4. dry with materialNo further drying of the acetylene gas
5. customafter 1 hour
6. customof flushing the gas through), the solution
7. temperatureto maintain the temperature
8. customvery close to −78° C
9. additionAfter this addition
10. temperatureThe temperature was maintained for an additional 1 hour
11. customThe reaction was quenched by the slow addition of a small amount of saturated ammonium chloride (about 5 mL) and additional water (50 mL)
12. additionPentane (100 mL) was added
13. customthe organic layer was separated
14. extractionThe aqueous layer was extracted a second time with pentane (50 mL)
15. customthe organic layer separated
16. washThe organic layers were washed with water (3×50 mL)
17. dry with materialdried over MgSO4
18. filtrationfiltered
19. concentrationconcentrated on the rotary evaporator
20. customNo further purification

ORD record

ord-2837bf0bfd774baaafd9067996b2466b

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08779179B2