Water → 3-Hydroxy-3-methyl-1-decene

Temperature

-20 °C

BK1114. Trimethylsulfonium iodide (23.53 g, 115.3 mmol) was suspended in anhydrous THF (250 mL) under argon and the slurry cooled to −20° C. A pre-cooled (−20° C.) solution of n-BuLi (2.14M in hexanes, 51.2 mL, 109 mmol) was added slowly via cannulating needle and the solution stirred for 10 minutes at −20° C. A pre-cooled (−20° C.) solution 2-nonanone (5.0 mL, 28.8 mmol) was then added slowly via cannulating needle and the resultant solution was stirred at −20° C. for 1 hour. The reaction was allowed to warm to room temperature over 2 hours. Water (200 mL) was added and the mixture was extracted with Et2O (3×100 mL). The combined organics were dried over MgSO4, filtered and concentrated in vacuo to afford an oily residue. This material was chromatographed on silica gel (eluting with 10% EtOAc/hexanes) to afford 3-hydroxy-3-methyl-1-decene (3.56 g, 72% yield) as a colorless oil.

1. additionwas added slowly
2. additionwas then added slowly
3. temperatureto warm to room temperature over 2 hours
4. extractionthe mixture was extracted with Et2O (3×100 mL)
5. dry with materialThe combined organics were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto afford an oily residue
9. customThis material was chromatographed on silica gel (eluting with 10% EtOAc/hexanes)

ORD record

ord-f0c6f6d212d64e738c06ef354c0817a6

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08013015B2