Tetrabutylammonium Fluoride → HCID 18972191, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (0.58 mL of a 1.0M solution in THF, 0.58 mmol) was added to (±)-methyl-5-[[6-(1-t-butyldimethylsilyloxy-3-(2-thienyl)propyl)]-1,3-benzodioxolyl]pentanoate (Compound E, 178 mg, 0.36 mmol) in THF (4.5 mL). After 16 hours the reaction was diluted with EtOAc and washed with H2O. The organic portion was dried (MgSO4) filtered and concentrated in vacuo. Flash column chromatography (silica gel, 2:1 hex/EtOAc) gave 135 mg (99%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 7.14 (d, J=5.1 Hz, 1H), 7.01 (s, 1H), 6.93 (dd, J=3.3, 5.1 Hz, 1H), 6.83 (d, J=3.3 Hz, 1H), 6.60 (s, 1H), 5.92 (s, 2H), 4.88-4.91 (m, 1H), 3.67 (s, 3H), 2.96-3.03 (m, 2H), 2.43-2.49 (m, 2H), 2.29 (t, J=6.9 Hz, 2H), 1.88-2.20 (m, 2H), 1.80 (d, J=3.0 Hz, 1H), 1.44-1.66 (m, 4H).

Provenance & Evidence