3-Thiopheneethanol

Clear colorless to yellowish-brown liquid

Step 2: 2-(thiophen-3-yl)ethanol Tetrahydrofuran (200 mL) was added to LiAlHIn a flame-dried Schlenk flask, equipped with a magnetic stirring bar, an argon inlet, and a septum, LiAlH4 (5.7 g, 150 mmol, 1.5 equiv) was dissolved in THF (100 mL) at 0 °C. A solution of 3-thienylacetic acid (3, 14.2 g, 100 mmol, 1.0 equiv) in THF (50 mL) at 0 °C was added dropwise. The mixture was stirred for 3 h at 0 °C and then it was carefully quenched with EtOAc and EtOH. Subsequently, 1–2percent NaOH (20 mL) was added and the mixture was stirred for 1 h, allowing aluminum hydroxide to precipitate as a granular solid. Finally, the mixture was filtered over Celite. The collected organic layers were dried (MgSO4), and the solvent was evaporated in vacuo to give the pure alcohol 4 (12.5 g, 98percent) as a pale yellow oil.To a 0 C cooled stirred suspension of lithium aluminiumhydride (8.0 g, 0.21 mol) in THF (100 mL) was added 3-Thiopheneaceticacid 01 (20 g, 0.14 mol) in THF (100 mL) drop wise over1 h. Reaction mixture was warmed to room temperature and stirredfor 6 h. Reaction progress was checked by TLC for completionand then quenched with 10percent NaOH solution. The mixture was filteredover Celite, washed with ethylacetate. Aqueous layer wasextracted with ethylacetate and the combined organic layer waswashed with brine. Dried over sodium sulfate and concentratedto yield 2 as a yellow liquid (14.2 g, 78percent) 1H NMR (MeOD, 400MHz): d 5.92–5.87 (m, 1H), 5.69–5.66 (m, 1H), 5.57 (s, 1H) 2.90(d, J = 14.0 Hz, 1H), 2.38 (d, J = 14 Hz, 1H), 1.55–1.42 (m, 2H). 13CNMR (DMSO d6, 100 MHz): 145.53, 129.13, 126.54, 121.45, 64.46, 38.85; ESI-MS m/z: (Calcd for C6H8OS: 128.03); Found:128.9 [M+H]+.Step 1: 2-(3-Thienyl)ethanol [00367] A solution of thiophene-3-acetic acid (4.982 g, 35.04 mmol) in THF ( 120 mL, 1500 mmol) was cooled to 0 °C, and lithium tetrahydroaluminate ( 1 .596 g, 42.05 mmol) was added slowly over 15 min. The reaction was allowed to warm to rt and stirred for 2hrs. The reaction was quenched via addition of water (5 mL) and EtOAc ( 10ml). The mixture was filtered, and the filter cake was washed with 30ml EtOAc. The filtrate was concentrated in vacuo to afford the title compound (3.59 g). NMR (400 MHz, Chloroform-d) δ 7.31 (dd, J = 4.9, 3.0 Hz, 1 H), 7.1 1 - 7.05 (m, 1 H), 7.05 - 6.97 (m, 1 H), 3.87 (t, J = 6.4 Hz, 2H), 2.92 (t, J = 6.4 Hz, 2H), 1.71 (s, 1 H).

Molecular Weight:128.19
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:128.02958605
Monoisotopic Mass:128.02958605
Topological Polar Surface Area:48.5
Heavy Atom Count:8
Complexity:65.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes