Reaction #607843

Reaction equation

linalool

linalool

→

linalool

1-methylcyclopent-2-enol

Conditions

Workup

1. 1
   Otherthe required amount was removed in a round bottom flask
2. 2
   workup.ADDITIONcharged with a stirbar
3. 3
   Othersealed with a septum
4. 4
   OtherLinalool was transferred via syringe into the RBF
5. 5
   workup.ADDITIONcontaining the catalyst
6. 6
   Othervigorous bubbling
7. 7
   workup.WAITThe bubbling continued for 30-45 minutes
8. 8
   OtherOnce bubbling
9. 9
   Otherwas bubbled into the reaction mixture for 15 minutes
10. 10
    Other1H NMR of the crude reaction mixture
11. 11
    Other(−78° C.)
12. 12
    OtherAfter transfer the product was sealed under nitrogen
13. 13
    Otherstored at room temperature

Procedure

Example 1, general preparative scale procedure for synthesis of 1 from linalool: Reactions were run with 0.1 mol % of the Hoveyda-Grubbs 2nd generation catalyst. The catalyst was stored in the glove box and the required amount was removed in a round bottom flask charged with a stirbar, and sealed with a septum. Linalool was transferred via syringe into the RBF containing the catalyst. At this point the flask was vented through an oil bubbler and within 30 seconds vigorous bubbling began while stirring at room temperature. The bubbling continued for 30-45 minutes and then ceased. Once bubbling had stopped air was bubbled into the reaction mixture for 15 minutes to ensure the catalyst was inactive. 1H NMR of the crude reaction mixture showed 100% conversion of starting linalool. The product was immediately vacuum transferred (1 torr) to a chilled flask (−78° C.). After transfer the product was sealed under nitrogen and stored at room temperature. The product was analyzed via NMR. 1H NMR (CDCl)Cl3) δ: 1.29 (s, 3H), 1.84 (m, 2H), 2.23 (m, 1H), 2.37 (m, 1H), 2.57 (broad s, 1H), 5.65 (m, 214). FIG. 3. Representative 1H NMR of 1-methylcyclopent-2-enol produced by RCM of linalool.

Source