Reaction #47100

Reaction equation

1-hexyn-3-ol

ethyl diazoacetate

→

product 446

Yield 54.3%

(1-Ethynylbutoxy)acetic acid ethyl ester

Yield 54.3%

Solvents

heptane

dichloromethane

Conditions

Workup

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

Procedure

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)

Source