Reaktion #47100

Reaktionsgleichung

1-hexyn-3-ol

ethyl diazoacetate

→

product 446

Ausbeute 54.3%

(1-Ethynylbutoxy)acetic acid ethyl ester

Ausbeute 54.3%

Lösungsmittel

heptane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered
2. 2
   SonstigeThe filtrate is evaporated
3. 3
   Sonstigethe residue purified by chromatography on silica gel
4. 4
   Waschenelution with EtOAc:heptane (25:75)

Vorschrift

To a solution of 1-hexyn-3-ol (981 mg, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (1.0 mL, 9.0 mmol). The reaction mixture is stirred at rt for 6 h. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue purified by chromatography on silica gel: elution with EtOAc:heptane (25:75) gives 900 mg of the product 446. 1H NMR (CDCl3) δ 4.35-4.10 (m, 5 H), 2.43 (s, 1 H), 1.90-1.65 (m, 2 H), 1.65-1.40 (m, 2 H), 1.40-1.20 (m, 3 H), 0.95 (t, 3 H)

Quelle