Lithium Hydroxide → 1-(5-Ethynyl-2-thienyl)-2,2,2-trifluoroethanone
Reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([C:5]1[S:6][C:7]([C:10]#[C:11][Si](C)(C)C)=[CH:8][CH:9]=1)=[O:4].[Li+].[OH-]>C1COCC1.O>[C:10]([C:7]1[S:6][C:5]([C:3](=[O:4])[C:2]([F:1])([F:17])[F:16])=[CH:9][CH:8]=1)#[CH:11]Participants
5
Procedure
To a stirred solution of D1 (1.0 eq) in THF (0.1 M) at RT was added a solution of LiOH (2.0 eq) in H2O (0.1 M) and the reaction mixture was stirred for 1 hr, then quenched by adding 6M HCl solution until pH=2. The organic solvent was evaporated and the product was extracted by DCM. Organic layers were washed with brine and dried (Na2SO4). Evaporation of the solvent under reduced pressure gave the crude product which was purified by flash column chromatography using Pentane to yield the desired compound as a brown oil. 1H NMR (300 MHz, CDCl3, 300K) δ 7.85-7.80 (1H, m), 7.32 (1H, d, J=4.2 Hz), 3.66 (1H, s).