Carbon Dioxide → HCID 14013750, compound

Temperature

-78 °C

To 50 ml of dry THF at -78° C. was added 6.3 ml (0.045 mol) of diisopropylamine followed by 19 ml (0.043 mol) of 2.3M n-butyllithium in hexane. After stirring at -78° C. for 15 minutes, a solution of 13.0 g (0.036 mol) of product of Example 8 in 50 ml of dry THF was added. After stirring at -78° C. for one hour, small pieces of dry ice were added. The addition was stopped when the exotherm ceased. Stirring at -78° C. was continued for 1 hour and then the reaction mixture was allowed to warm up to room temperature in 11/2 hour. The reaction mixture was poured into 450 ml of H2O containing 50 ml of concentrated HCl, extracted with ether, dried (MgSO4) and concentrated in vacuo to a dark oil. This oil, 5.5 g (0.040 mol) of K2CO3 and 11.2 ml (0.180 mol) of methyl iodide in 125 ml of acetone was refluxed for 17 hours. The cooled reaction mixture was concentrated in vacuo. The residue was poured into water, extracted with ether, dried (MgSO4) and concentrated in vacuo to a dark oil which was kugelrohr distilled at 51 Pa, pot temperature 90° C., to give 11.01 g (72.9%) of product as a yellow oil, nD25 1.4484.

1. stirringAfter stirring at -78° C. for one hour
2. additionThe addition
3. stirringStirring at -78° C.
4. waitwas continued for 1 hour
5. temperatureto warm up to room temperature in 11/2 hour
6. extractionextracted with ether
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo to a dark oil
9. customThe cooled reaction mixture
10. concentrationwas concentrated in vacuo
11. additionThe residue was poured into water
12. extractionextracted with ether
13. dry with materialdried (MgSO4)
14. concentrationconcentrated in vacuo to a dark oil which
15. distillationwas kugelrohr distilled at 51 Pa, pot temperature 90° C.

ORD record

ord-d48dd2246aec40429eb4b0afa70f6d37

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04921530