Toluene → HCID 66696968, 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 form “3-ethylbicyclo[3.2.0]hept-6-en-6-one” in the reaction solution. 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 filtered. The filtrate was added to a reaction solution prepared by adding sodium hydride (>65% oil, 761.9 mg, 20 mmol) to a solution of tert-butyl dimethoxyphosphorylacetate (4.48 g, 20 mmol) in tetrahydrofuran (50 mL) 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. The 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. customThe mixture was separated into aqueous and organic layers
2. additionby the addition of saturated saline (50 mL) and toluene (20 mL)
3. washThen, the organic layer was washed with a 1 N aqueous sodium hydroxide solution and saturated saline in this order
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. additionThe filtrate was added to a reaction solution
7. customprepared
8. stirringthe mixture was further stirred for 1 hour
9. customThe reaction solution was separated into aqueous and organic layers
10. additionby the addition of a saturated aqueous solution of ammonium chloride and saturated saline
11. extractionThe aqueous layer was subjected to extraction with ethyl acetate
12. washwashed with saturated saline
13. dry with materialdried over anhydrous magnesium sulfate
14. distillationThe solvent was distilled off under reduced pressure
15. customthe residue was purified by silica gel column chromatography
16. customto obtain the compound of interest as a pale yellow oil substance (1.32 g, 31%, E/Z mixture)

ORD record

ord-168f1750a4b14dcda1ad606137c3aa91

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09162971B2