Water → HCID 23043534, compound

To 564.3 ml of 1M diborane in tetrahydrofuran was added, at 0° C. under argon with stirring, 79.16 g of 2-methyl-2-butene. After stirring for 1/2 hour, 65 g of 8-[2-(2-methoxyethoxy]-2-octene was added. This mixture was stirred one hour at room temperature, then 700 ml of 1M diborane in tetrahydrofuran was added over a period of 1.5 hours. The mixture was then stirred 2 hours, then water was added and about 2/3 of the tetrahydrofuran removed. The remainder was stirred in an ice bath as 150 ml of 3N sodium hydroxide was added, followed by the slow addition of 150 ml of 30% hydrogen peroxide. After stirring 1/2 hour the mixture was extracted with ether. The ether extract was washed in succession with saturated aqueous sodium chloride, saturated aqueous sodium bisulfite, saturated aqueous sodium chloride, then dried and the solvent removed. The residue was distilled on a Kugelrohr apparatus. The fraction boiling at 90°-110° C., 0.2 mm was discarded. The fraction boiling at 160°-180° C., 0.2 mm was collected giving 41.3 g of the desired compound as a clear liquid.

1. stirringAfter stirring for 1/2 hour
2. stirringThis mixture was stirred one hour at room temperature
3. stirringThe mixture was then stirred 2 hours
4. customremoved
5. stirringThe remainder was stirred in an ice bath as 150 ml of 3N sodium hydroxide
6. additionwas added
7. additionfollowed by the slow addition of 150 ml of 30% hydrogen peroxide
8. stirringAfter stirring 1/2 hour the mixture
9. extractionwas extracted with ether
10. extractionThe ether extract
11. washwas washed in succession with saturated aqueous sodium chloride, saturated aqueous sodium bisulfite, saturated aqueous sodium chloride
12. customdried
13. customthe solvent removed
14. distillationThe residue was distilled on a Kugelrohr apparatus
15. customThe fraction boiling at 160°-180° C., 0.2 mm was collected

ORD record

ord-484d6a57fba94368921fc501f277ca44

Source dataset

uspto-grants-1990_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04939127