Reaktion #50482

Reaktionsgleichung

Example 1

6-Methyl-5-hepten-1-yne

chloride

HMPA

hexane EtOAc

→

title compound

Ausbeute 74.0%

(E)-6,10-Dimethyl-5,9-undecadien-1-ol

Ausbeute 74.0%

Lösungsmittel

THF

hexane ether

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat 0° C.
2. 2
   workup.ADDITIONAfter addition
3. 3
   Sonstigequenched with 1N HCl solution
4. 4
   WaschenTHe organic layer was washed with 1N HCl
5. 5
   Trocknendried over MgSO4
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto provide 3.59 g of crude oil
8. 8
   Wascheneluted with 7:1 hexane/ EtOAc collecting 30 mL fractions
9. 9
   Sonstigeevaporated

Vorschrift

A solution of 198 mL (58.0 mmol) of 0.29M Example 1, Part B-(2) Grignard reagent in THF and 48 mL (275.9 mmol) of HMPA at 0° C. under argon was treated dropwise with 2.0 g (11.6 mmol) of Example 6, Part A chloride in 20 mL of THF. After addition, the reaction was allowed to warm to room temperature for 2 hours, at which point the reaction was diluted with 1:1 hexane/ether and quenched with 1N HCl solution. THe organic layer was washed with 1N HCl followed by water, saturated sodium bicarbonate, brine, dried over MgSO4 and evaporated to provide 3.59 g of crude oil. Flash chromatography was performed on 360 g of silica gel packed and loaded with 10:1 hexane/EtOAc and eluted with 7:1 hexane/ EtOAc collecting 30 mL fractions. Fractions 32 to 49 were combined and evaporated to provide 1.68 g (74%) of title compound in the form of an oil.

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