Hexane → 1-Cycloheptyl-3-(trimethylsilyl)-2-propyn-1-one

Temperature

-10 °C

To a solution of triethylsilylacetylene (4.78 ml, 14 mmol) in THF (10 ml) at −78° C. was added dropwise a solution of BuLi in hexane (8 ml, 13 mmol). After 30 minutes, the mixture was warmed to −10° C. and a solution of N-methoxy-N-methylcycloheptanecarboxamide (2 g, 10.8 mmol) in THF (10 ml) was added. The mixture was stirred for 30 minutes at −10° C., quenched by addition of aqueous saturated ammonium chloride, allowed to warm up to room temperature and diluted with ether. The layers were separated and the aqueous phase was extracted with ether. Combined organic layers were washed with brine, dried over Na2SO4 and concentrated. After purification by chromatography on silica gel (hexane/CH2Cl2 90/10), the 1-cycloheptyl-3-(trimethylsilyl)-2-propyn-1-one 28 was obtained as a colorless liquid (1.74 g, 72%).

1. customquenched by addition of aqueous saturated ammonium chloride
2. temperatureto warm up to room temperature
3. additiondiluted with ether
4. customThe layers were separated
5. extractionthe aqueous phase was extracted with ether
6. washCombined organic layers were washed with brine
7. dry with materialdried over Na2SO4
8. concentrationconcentrated
9. customAfter purification by chromatography on silica gel (hexane/CH2Cl2 90/10)

ORD record

ord-2e7a6b3e1c5e4e45bdc476bd32dac3ab

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361668B2