5-(HydroxyMethyl)thiophene-2-carbonitrile synthesis

5synthesis methods

Product Name:5-(HydroxyMethyl)thiophene-2-carbonitrile
CAS Number:172349-09-6
Molecular formula:C6H5NOS
Molecular Weight:139.18

21512-16-3 Synthesis

21512-16-3
91 suppliers
$8.00/100mg

5-(HydroxyMethyl)thiophene-2-carbonitrile

172349-09-6
31 suppliers
inquiry

Yield: 6.1 g (88%)

Reaction Conditions:

with sodium borohydrid in ethanol

Steps:

61.B B)
B) Preparation of 2-cyano-5-(hydroxymethyl)thiophene To a solution of 2-cyano-5-formyl-thiophene (6.9 g, 50 mmol) in EtOH (100 mL) was added sodium borohydride (1.9 g, 50 mmol) in portions. After 5 min of stirring, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and brine. The layers were separated and the organic phase was washed once with 1M citric acid and once with brine, then dried (MgSO₄), filtered and concentrated in vacuo to give 6.1 g (88%) of 2-cyano-5-(hydroxymethyl)thiophene. ¹ H NMR FD-MS, m/e 140 (M⁺) Analysis for C₆ H₅ NOS: Calc: C, 51.78; H, 3.62; N, 10.06; Found: C, 51.54; H, 3.62; N, 9.86.

References:

Eli Lilly and Company US5914319, 1999, A

557-21-1 Synthesis