Reaction #47103

Reaction equation

1,3-dioxan-5-ol

ethyl diazoacetate

→

product 454

Yield 41.3%

(1,3-Dioxan-5-yl)acetic acid ethyl ester

Yield 41.3%

Solvents

heptane

dichloromethane

Conditions

Workup

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

Procedure

To a solution of 1,3-dioxan-5-ol (1.04 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 4 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 (1:4) gives 0.65 g of the product 454. 1H NMR (CDCl3) δ 5.04 (s, 1 H), 4.89 (s, 1 H), 4.25-4.20 (m, 5 H), 3.98 (dd, 1 H), 3.78 (dd, 1 H), 3.65 (d, 1 H), 1.29 (t, 3 H).

Source