Sodium hydride → HCID 86646122, compound

4-Ethyl-3-hydroxyhept-6-enoic acid (3.13 g, 18.2 mmol) was dissolved in acetic anhydride (15 mL). To the solution, potassium acetate (4.27 g, 43.6 mmol) was added, and the mixture was stirred at room temperature for 100 minutes. The reaction solution was heated to reflux and stirred for 3.5 hours. To the reaction solution, ice water and toluene were then added, and this mixture was stirred overnight at room temperature. The mixture was separated into aqueous and organic layers by the addition of saturated saline (50 mL) and toluene (20 mL). Then, the organic layer was washed with a 1 N aqueous sodium hydroxide solution and saturated saline in this order, then dried over anhydrous magnesium sulfate, and then filtered. This filtrate was added to a reaction solution prepared by adding sodium hydride (>65% oil, 761.9 mg, 20 mmol) to a tetrahydrofuran solution (50 mL) of tert-butyl dimethoxyphosphorylacetate (4.48 g, 20 mmol) under ice cooling, and the mixture was further stirred for 1 hour. The reaction solution was separated into aqueous and organic layers by the addition of a saturated aqueous solution of ammonium chloride and saturated saline. The aqueous layer was subjected to extraction with ethyl acetate. These organic layers were combined, then washed with saturated saline, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the compound of interest as a pale yellow oil substance (1.32 g, 31%, E/Z mixture).

1. temperatureThe reaction solution was heated
2. temperatureto reflux
3. stirringstirred for 3.5 hours
4. stirringthis mixture was stirred overnight at room temperature
5. customThe mixture was separated into aqueous and organic layers
6. additionby the addition of saturated saline (50 mL) and toluene (20 mL)
7. washThen, the organic layer was washed with a 1 N aqueous sodium hydroxide solution and saturated saline in this order
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. additionThis filtrate was added to a reaction solution
11. customprepared
12. stirringthe mixture was further stirred for 1 hour
13. customThe reaction solution was separated into aqueous and organic layers
14. additionby the addition of a saturated aqueous solution of ammonium chloride and saturated saline
15. extractionThe aqueous layer was subjected to extraction with ethyl acetate
16. washwashed with saturated saline
17. dry with materialdried over anhydrous magnesium sulfate
18. distillationThe solvent was distilled off under reduced pressure
19. customthe residue was purified by silica gel column chromatography
20. customto obtain the compound of interest as a pale yellow oil substance (1.32 g, 31%, E/Z mixture)

ORD record

ord-6ee3e9cc4b9e4c838da28c0d2c47344d

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947738B2