Ammonium Chloride → HCID 54180765, compound

To 5.2 ml of a 1.6M n-hexane solution of n-butyl lithium was added 15 ml of anhydrous THF at -78° C. (bath temperature) in a nitrogen atmosphere, and 1.3 g of a tetrahydropyranyl ether of 3-butyn-3-ol was added dropwise thereto under the same conditions over 10 minutes. After the addition, the mixture was stirred for 30 minutes. Then, 20 ml of an anhydrous THF solution containing 2.1 g of 2,4-bis(trimethylsiloxy)-2,5,5-trimethylcyclohexanone was added dropwise to the mixture under the same conditions over 20 minutes. After the dropwise addition, the mixture was stirred for 5 hours. A saturated ammonium chloride aqueous solution was added to the reaction mixture, and the mixture was extracted with diethyl ether. After the diethyl ether was removed from the extract by distillation, a 1N hydrochloric acid aqueous solution and methanol were added to the residue, followed by stirring at room temperature for 5 hours. The methanol was removed by distillation under reduced pressure, and the residue was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, and the solvent, etc. were removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.1 g (yield: 70%) of 4-(1,2,4-trihydroxy-2,5,5-trimethylcyclopentyl)but-3-en-2-ol.

1. additionwas added dropwise
2. additionAfter the addition
3. additionwas added dropwise to the mixture under the same conditions over 20 minutes
4. additionAfter the dropwise addition
5. stirringthe mixture was stirred for 5 hours
6. extractionthe mixture was extracted with diethyl ether
7. customAfter the diethyl ether was removed from the
8. extractionextract by distillation
9. additiona 1N hydrochloric acid aqueous solution and methanol were added to the residue
10. stirringby stirring at room temperature for 5 hours
11. customThe methanol was removed by distillation under reduced pressure
12. extractionthe residue was extracted with diethyl ether
13. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
14. customthe solvent, etc. were removed by distillation under reduced pressure
15. customThe residue was purified by silica gel column chromatography

ORD record

ord-16528901963e4acd986438438336e44e

Source dataset

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04983723