Tetrahydrofuran → HCID 14793448, compound

Temperature

0 °C

A mixture of 1.25 g (8.1 mM) of (-)-2-methylhexanoic acid ([α]D26 -6.15 degrees (c 1.073, methanol)), 20 ml of dry tetrahydrofuran and 0.90 g (8.9 mM) of dry triethylamine was cooled on an ice bath, and 0.84 g (8.1 mM) of ethyl chloroformic acid was added dropwise thereto in 5 minutes, followed by 1 hour of stirring at 0° C. A white salt precipitated at this time was removed by filtration. To a mixture of 0.46 g (12.1 mM) of sodium borohydride and 8 ml of distilled water under stirring at 0° C., the above filtrate was added dropwise in 20 min., followed by stirring at room temperature for 3 hours. After the reaction, 2N-hydrochloric acid was added to give pH 1, and the organic layer was separated. The remaining aqueous layer was subjected to extraction with ether, and the ether extract was mixed with the organic layer. The mixture was washed with 1N-sodium bicarbonate aqueous solution and dried on sodium sulfate. After the removal of solvent by distillation, the product was subjected to distillation by a Kugelrohr distiller. At 95° C./4 mmHg, (+)-2-cyano-2-methyl-1-hexanol was obtained in an amount of 0.55 g (Yield:48.5%), [α]D26 +0.66 degree (c 1.823, ether).

1. temperaturewas cooled on an ice bath
2. waitfollowed by 1 hour
3. customA white salt precipitated at this time
4. customwas removed by filtration
5. additionTo a mixture of 0.46 g (12.1 mM) of sodium borohydride and 8 ml of distilled water
6. stirringunder stirring at 0° C.
7. additionthe above filtrate was added dropwise in 20 min.
8. stirringby stirring at room temperature for 3 hours
9. customAfter the reaction, 2N-hydrochloric acid
10. additionwas added
11. customto give pH 1
12. customthe organic layer was separated
13. extractionThe remaining aqueous layer was subjected to extraction with ether
14. extractionthe ether extract
15. additionwas mixed with the organic layer
16. washThe mixture was washed with 1N-sodium bicarbonate aqueous solution
17. customdried on sodium sulfate
18. customAfter the removal of solvent
19. distillationby distillation
20. distillationthe product was subjected to distillation by a Kugelrohr distiller

ORD record

ord-e531324f190d4ad3b38c084f70c7c173

Source dataset

uspto-grants-1991_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04999130