Reaktion #47102

Reaktionsgleichung

1-cyclopentylethan-1-ol

ethyl diazoacetate

→

product 452

Ausbeute 44.8%

(1-Cyclopentylethoxy)acetic acid ethyl ester

Ausbeute 44.8%

Lösungsmittel

heptane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   SonstigeThe filtrate is evaporated
3. 3
   Sonstigethe residue is purified by chromatography on silica gel
4. 4
   Waschenelution with EtOAc:heptane (1:9)

Vorschrift

To a solution of 1-cyclopentylethan-1-ol (1.14 g, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.03 mmol). The reaction mixture is stirred at rt for 0.5 h. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue is purified by chromatography on silica gel; elution with EtOAc:heptane (1:9) gives 0.81 g of the product 452. 1H NMR (CDCl3) δ 4.30-4.15 (m, 2 H), 4.09 (d, 2 H), 3.25-3.15 (m, 1 H), 2.00-1.78 (m, 2 H), 1.75-1.35 (m, 6 H), 1.29 (t, 3 H), 1.15 (d, 3 H).

Quelle