1-HYDROXYMETHYL-3-CYCLOPENTENE

(a) cyclopent-3-enylmethanol (0164) (0165) To a suspension of lithium aluminum hydride (0.5083 g, 13.37 mmol, 3eq) in dry 100 ml THF at −78° C., cyclopent-3-enecarboxylic acid (0.5000 g, 4.45 mmol) was added drop wise over 1 h. The mixture was stirred for 6 h, and then quenched with 15 ml 1M NaOH. Mixture was stirred for an additional 2 h, then concentrated and up taken in diethyl ether and dried over MgSOTo a solution of 2 (8.6 g, 68 mmol) in THF (40.0 mL) at 0° C. was added LAH (54 mL, 1M solution in THF) under NTo a suspension of lithium aluminum hydride (15.2g, 0.40 mol) in anhydrous ether (1 L) at 0°C under nitrogen, was added the solution of methyl cyclopent-3-enecarboxylate (50 g, 0.40 mol) in ether (300 mL) dropwise over 5 hrs. The suspension was stirred at room temperature overnight. TLC indicated the completion of the reaction. The reaction was re-cooled to 0°C. Saturated solution of NaTo a cold (—78° C.) solution of 703 (7 g, 50 mmol) in dry THF (150 mE) was added EiA1H4 (1 M soln in THF, 25 mE, 25 mmol), and the reaction solution was stirred at —78° C.under argon for 4 h. Then the reaction solution was allowed towarm to 0° C., and 2.5 mE of water, 2.5 mE of 15percent NaOH, and 7.5 mE of water were added sequentially. Afier warming to tt., the precipitates were filtered through a celite, and the celite was washed with hot EtOAc. The combined filtrateswere washed with 0.1 N NaOH, and brine, dried (MgSO4), filtered, concentrated and dried in vacuo to give 4.294 g(84percent) of 704 as a pale yellow liquid. ‘H NMR (400 MHz, CDC13) ö 5.68 (s, 2H, 2CH=CH), 3.57 (d, J=6.0 Hz, 2H, CH2OH), 2.54-2.48 (m, 3H, CH+CH2), 2.15-2.10 (m, 2H, CH2).To a cold (-78 C.) solution of 703 (7 g, 50 mmol) in dry THF (150 mE) was added EiA1H4 (1 M soln in THF, 25 mE, 25 mmol), and the reaction solution was stirred at -78 C.under argon for 4 h. Then the reaction solution was allowed towarm to 0 C., and 2.5 mE of water, 2.5 mE of 15% NaOH, and 7.5 mE of water were added sequentially. Afier warming to tt., the precipitates were filtered through a celite, and the celite was washed with hot EtOAc. The combined filtrateswere washed with 0.1 N NaOH, and brine, dried (MgSO4), filtered, concentrated and dried in vacuo to give 4.294 g(84%) of 704 as a pale yellow liquid. 'H NMR (400 MHz, CDC13) oe 5.68 (s, 2H, 2CH=CH), 3.57 (d, J=6.0 Hz, 2H, CH2OH), 2.54-2.48 (m, 3H, CH+CH2), 2.15-2.10 (m, 2H, CH2).Step A : Preparation of 3-cyclopentenylmethanol 0.78 mol (109.45 g) of 3-cyclopentenylcarboxylic acid ethyl ester dissolved in 400 ml of anhydrous ether are added dropwise to a stirred suspension of 24 g of lithium aluminum hydride (0.7 mmol) in 500 ml of anhydrous ether. The reaction mixture is stirred at 20C for 3 hours and hydrolized by careful addition of 24 ml of water, 24 ml of 15% aqueous sodium hydroxide and three times 24 ml of water. The white precipitate is discarded by filtration and the filtrate is washed twice with brine, dried over sodium sulfate, filtered and evaporated to give 67.5 g of the product 3-cyclopentenylmethanol (88% yield) which is used in the next step without further purification.

Molecular Weight:98.14
XLogP3:1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:98.073164938
Monoisotopic Mass:98.073164938
Topological Polar Surface Area:20.2
Heavy Atom Count:7
Complexity:68.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes