1-HYDROXYMETHYL-3-CYCLOPENTENE

7686-77-3

25125-21-7

General procedure for the synthesis of 1-hydroxymethyl-3-cyclopentene from 3-cyclopentenecarboxylic acid: (a) To an anhydrous tetrahydrofuran (100 ml) suspension of lithium aluminium hydride (0.5083 g, 13.37 mmol, 3 eq.), a solution of 3-cyclopentenecarboxylic acid (0.5000 g, 4.45 mmol) was slowly added dropwise at -78°C for a controlled duration of 1 hours. The reaction mixture was stirred continuously at this temperature for 6 h. The reaction was subsequently quenched with 15 ml of 1 M NaOH solution. After continued stirring for 2 h, the reaction mixture was concentrated, washed with ether and dried with anhydrous magnesium sulfate to give the final clarified liquid product cyclopent-3-enylmethanol (3.79 mmol, molecular weight 98.14 g/mol, 85% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 2.12-2.16 (tttt, 1H), 2.49-2.53 (dd, 2H), 3.57-3.58 (d, 3H, J=5.14 Hz), 5.69 (s, 2H).