Acetylene → HCID 131717921, compound

Temperature

-78 °C

A solution of 1.15 g (6.54 mmol) of Example 16, Part A acetylene in 15 mL of THF at -78° C. under argon was treated with 4.5 mL (7.19 mmol) of 1.6 M n-butyllithium in hexanes over 10 minutes to give a purple solution. The reaction was allowed to stir at -78° C. for 1 hour when 1 mL (13.1 mmol) of methyl chloroformate was added to give a yellow solution. The reaction was allowed to stir at -78° C. for 1 hour when it was quenched with saturated NH4Cl and diluted with diethyl ether. The ether extract was washed with water, saturated NaHCO3, brine, dried over MgSO4 and evaporated to provide 1.73 g of a crude yellow oil. Flash chromatography was performed on 180 g of silica gel packed and loaded with 25:1 hexane/EtOAc and eluted with 20:1 hexane/EtOAc collecting 20 mL fractions. Fractions 59 to 83 were combined and evaporated to provide 1.34 g (87%) of title compound in the form of a pale yellow oil.

1. customat -78° C.
2. customto give a purple solution
3. additionwas added
4. customto give a yellow solution
5. customwas quenched with saturated NH4Cl
6. additiondiluted with diethyl ether
7. extractionThe ether extract
8. washwas washed with water, saturated NaHCO3, brine
9. dry with materialdried over MgSO4
10. customevaporated
11. customto provide 1.73 g of a crude yellow oil
12. washeluted with 20:1 hexane/EtOAc collecting 20 mL fractions
13. customevaporated

ORD record

ord-001bd66e58b24c2a9c7c49a2122b5bdc

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05273969