Formic Acid → HCID 14218637, compound

Participants

Reaction Steps

A mixture of the product of Procedure 13 (62.7 g, 0.076 mol) and 90% aqueous formic acid (110 ml) was stirred at room temperature for 1 hr. The reaction mixture was diluted with EtOAc (600 ml) and ice-water (300 ml) and the lower layer was adjusted to pH 3.3 with 30% aq. NaOH under vigorous stirring. The upper layer was diluted to 2 L, separated, washed with water (500 ml×3) and brine, dried over MgSO4 and concentrated under diminished pressure. The residue was dissolved in toluene (300 ml) which was carefully transferred to the top surface of a silica gel column (Wakogel C-200, 800 g). The column was eluted with CH2Cl2, 0.5%, 1.0%, 1.5%, 2.0% and 3.0% MeOH in CH2Cl2, successively. The fractions which exhibited approximately Rf: 0.12 on TLC (SiO2, 5% MeOH-CH were combined and concentrated in vacuo to give 30.0 g (68%) of the desired product as an amorphous powder. The starting material was recovered (8.4 g, 14%) from the fractions which showed Rf 0.55 on TLC.

Provenance & Evidence