Hexane → HCID 10922459, compound

Temperature

-78 °C

To a -78° C. solution of (Z)-1-ethoxy-2-tri-n -butylstannylethylene (17.85 g, 49.3 mmol) in anhydrous THF (250 ml) was added a solution of n-butyllithium in hexane (23.8 ml, 2.5M, 59.5 mmol) dropwise via syringe. The resulting solution was stirred at -78° C. for 1 hour, then a solution of 3-phenylcinnamaldehyde (7.0 g, 33.6 mmol) in anhydrous THF (100 ml) was added via syringe. The resulting bright purple solution was stirred at -78° C. for 4 hours, then allowed to warm to room temperature. The mixture was quenched with saturated aqueous sodium bicarbonate (200 ml), allowed to stir 10 minutes and diluted with water (300 ml). The phases were separated and the aqueous phase was extracted with ether. The combined organic phases were dried with anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 7.75 g of crude product. Purification by flash chromatography (1:3 ethyl acetate:hexane) gave 4.46 g (56.7% yield) of title product having properties identical to those of the preceding Preparation.

1. stirringThe resulting bright purple solution was stirred at -78° C. for 4 hours
2. temperatureto warm to room temperature
3. customThe mixture was quenched with saturated aqueous sodium bicarbonate (200 ml)
4. stirringto stir 10 minutes
5. additiondiluted with water (300 ml)
6. customThe phases were separated
7. extractionthe aqueous phase was extracted with ether
8. dry with materialThe combined organic phases were dried with anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give 7.75 g of crude product
12. customPurification by flash chromatography (1:3 ethyl acetate:hexane)

ORD record

ord-f5dfdb5bc8c64a549af07800b4a6f817

Source dataset

uspto-grants-1992_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05151545