Reaction #742292

Reaction equation

TMS-diazomethane

methanol

Hex-5-enoic acid

Trimethylsilyl diazomethane

→

Hex-5-enoic acid methyl ester

Solvents

diethyl ether

Conditions

Workup

1. 1
   Otherconsumption of the acid
2. 2
   OtherThe solvent was evaporated under reduced pressure carefully (product
3. 3
   WashThe solution was washed with saturated NaHCO3
4. 4
   Otherdried

Procedure

Hex-5-enoic acid methyl ester was prepared as follows. Hex-5-enoic acid (2.00 g, 17.5 mmol) was dissolved in diethyl ether (8 mL) and methanol (4 mL) and cooled to 0° C. To this solution was added 2.0 M Trimethylsilyl diazomethane (9 mL) dropwise. It was noted that a yellow TMS-diazomethane solution dissipates upon stirring with the reaction mixture, and the reaction is deemed complete when the yellow color persists. Caution should be observed, as the reaction is associated with vigorous gas evolution. When the yellow color persists in the reaction mixture, TLC analysis was conducted and confirmed consumption of the acid. The solvent was evaporated under reduced pressure carefully (product is somewhat volatile) and replaced with ethyl acetate. The solution was washed with saturated NaHCO3, dried, and the filtrate was used directly in the next step. 1H NMR (400 MHz) CDCl3 δ 5.45 (m, 1H), δ 4.9 (m, 2H), δ 3.65 (s, 3H), δ 2.20 (t, 2H), δ 2.05 (m, 2H), δ 1.70 (m, 2H).

Source