Triethylamine → HCID 91368801, compound

Temperature

80 °C

4-Allylhepta-2,6-dienoic acid (2.00 g, 12.0 mmol) was dissolved in benzene (5 mL). To the solution, oxalyl chloride (7.01 g, 55.2 mmol) was added under ice cooling, and the mixture was stirred in this state for 1 hour. The mixture was further stirred at room temperature for 30 minutes, then heated to 80° C., and stirred for 1 hour. Then, the solvent was distilled off under reduced pressure. To the residue, toluene was added, and the solvent was distilled off again under reduced pressure. The residue was dissolved in toluene (20 mL). This solution was added dropwise to a toluene solution (30 mL) of triethylamine (4.41 g, 43.68 mmol) heated in advance to reflux, and the mixture was further stirred for 2.5 hours. The reaction solution was allowed to cool, then diluted with saturated saline and ethyl acetate, and filtered through Xelite. The filtrate was separated into aqueous and organic layers. Then, the organic layer was washed with 1 N hydrochloric acid and saturated saline in this order, then dried over anhydrous magnesium sulfate, and then filtered. This filtrate was added to a reaction solution prepared in advance by adding sodium hydride (>65% oil, 457.1 mg, 12 mmol) to a tetrahydrofuran solution (20 mL) of tert-butyl dimethoxyphosphorylacetate (3.03 g, 12 mmol) under ice cooling, and the mixture was stirred for 1 hour. The solvent was distilled off under reduced pressure to obtain the compound of interest as a pale yellow oil substance (0.63 g, 16%, E/Z mixture).

1. stirringThe mixture was further stirred at room temperature for 30 minutes
2. stirringstirred for 1 hour
3. distillationThen, the solvent was distilled off under reduced pressure
4. additionTo the residue, toluene was added
5. distillationthe solvent was distilled off again under reduced pressure
6. dissolutionThe residue was dissolved in toluene (20 mL)
7. temperatureheated in advance
8. temperatureto reflux
9. stirringthe mixture was further stirred for 2.5 hours
10. temperatureto cool
11. filtrationfiltered through Xelite
12. customThe filtrate was separated into aqueous and organic layers
13. washThen, the organic layer was washed with 1 N hydrochloric acid and saturated saline in this order
14. dry with materialdried over anhydrous magnesium sulfate
15. filtrationfiltered
16. additionThis filtrate was added to a reaction solution
17. customprepared in advance
18. stirringthe mixture was stirred for 1 hour
19. distillationThe solvent was distilled off under reduced pressure
20. customto obtain the compound of interest as a pale yellow oil substance (0.63 g, 16%, E/Z mixture)

ORD record

ord-0887c56c37c14b15a07a9b91b276e893

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947738B2