Reaktion #79343

Reaktionsgleichung

H2O

1-bromo-5-methylhexane

methyl cyclopentanecarboxylate

LHMDS

→

oil

Ausbeute 21.1%

Methyl 1-(5-methylhexyl)cyclopentanecarboxylate

Ausbeute 21.1%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Extraktionwas extracted with CH2Cl2 (2×30 mL)
3. 3
   WaschenThe combined extracts were washed with water
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Sonstigepurified

Vorschrift

To a solution of methyl cyclopentanecarboxylate (300 mg, 2.3 mmol) in THF (20 ml) at −78° C. was added LHMDS (4.6 mL, 4.6 mmol) and stirred for 30 min, and followed by 1-bromo-5-methylhexane (626 mg, 3.5 mmol). The mixture was stirred from −78° C. to rt over 16 hr, before 30 ml of H2O was added and then was extracted with CH2Cl2 (2×30 mL). The combined extracts were washed with water, dried over MgSO4, filtered and concentrated, then purified using flash chromatography to give an oil (110 mg, 21%). MS [M+H]+333.

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