Hydrogen Peroxide → HCID 22000465, compound
Reaction equation
[F:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:3][CH:4]=[CH2:5].B.[O:13]1CCCC1.OO>>[F:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:3][CH2:4][CH2:5][OH:13]Participants
Procedure
The title compound was prepared essentially as described in Example 1. R-4-fluoro-1-methanesulfonoxydecane was prepared by copper catalyzed addition of vinyl magnesium bromide to epichlorohydrin to yield 5-chloro-4-hydroxypent-1-ene which was treated with base to give the corresponding epoxide. The epoxide is then ring opened by the addition of propyl magnesium bromide to yield 4-hydroxy-dec-1-ene. This hydroxy compound is converted to 4-fluoro-dec-1-ene as described in Example 1, followed by treatment with borane/tetrahydrofuran and hydrogen peroxide to give 4-fluoro-decanol. This alcohol was treated with methane sulfonyl chloride in the presence of triethylamine to yield the desired intermediate R-4-fluoro-1-methylsulfonoxy decane.
Sources & evidence
- ORD record
- ord-bc45de1b6c724a2aa157b5509e212403
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06139924
Reaction notes
Loading…