Synthesis
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).
References
[1] Tetrahedron, 2003, vol. 59, # 5, p. 671 - 676
[2] Journal of the American Chemical Society, 1982, vol. 104, p. 7105
[3] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 14, p. 2175 - 2178
[4] European Journal of Organic Chemistry, 2004, # 2, p. 289 - 303
[5] Journal of Heterocyclic Chemistry, 1989, vol. 26, # 2, p. 451 - 452
