Dimethyl Sulfide → HCID 131729881, compound

Participants

Reaction Conditions

Reaction Steps

4-Pentenoic acid (10.00 g, 99.88 mmol) was dissolved in methylene chloride (150 mL), and the mixture was cooled to −78° C. under N2(g). Ozone was bubbled through the reaction mixture, and the course of the reaction was monitored by TLC. After TLC showed disappearance of the starting material (ca. 2.5 h), methyl sulfide (15.0 mL, 205.23 mmol) was added and the reaction mixture was allowed to warm to room temperature. Subsequently, solvent was removed under reduced pressure, and the residue was dissolved in THF (200 mL). BocNHNH2 (13.2 g, 99.88 mmol) was then added, and the reaction mixture was refluxed overnight under Ar(g). Solvent was removed under reduced pressure, and the residue was purified by flash chromatography (silica gel, 6% v/v methanol in methylene chloride) to give BocNHN═CHCH2CH2CO2H as a white solid (13.60 g, 63%). HRMS (ESI) [M−H]− calcd for C9H15N2O4, 215.1032; found, 215.1035; 1H NMR (300 MHz, d6-DMSO) δ 12.16 (s, 1H), 10.45 (s, 1H), 7.30 (app bs, 1H), 2.45-2.30 (m, 4H), 1.41 (s, 9H); 13C NMR (100 MHz, d6-DMSO) δ 173.5, 152.4, 145.6, 78.9, 30.4, 28.1, 27.2.

Provenance & Evidence