5-methylnaphthalene-1,4-dione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Mercaptopropionic acid (0.69 mmol, 65 μL) was dissolved in 8 mL of water and cooled in an ice bath. This solution was added over 20-30 minutes to a solution of 5-methyl-1,4-naphthoquinone (0.69 mmole, 120 mg) dissolved in 15 mL of ethanol and cooled in an ice bath to form a reaction mixture. The reaction mixture was gradually allowed to warm to room temperature over a 1 hour period, and the ethanol was then allowed to evaporate. The crude product was purified via flash silica column chromatography (2:1 hexane:ethyl acetate with 1% v/v acetic acid) and provided a 70% yield of (5-methyl-1,4 naphthoquinonyl thio)- propionic acid, designated compound 1. 1H NMR data: (acetone-ds), δ 2.70 (s, 3H), 2.81 (t, J=7.2 Hz, 2H), 3.20 (t, J=7.2 Hz, 2H), 6.72 (s, 1H), 7.62 (d, J=7.5 Hz, 1H), 7.71 (t, J=7.5 Hz, 1H) 7.96 (d, J=Hz, 1H). LRMS m/z (rel. int.) 276 (M+, 30.5) 203 (100), 115 (68.2), 90 (41.0), 89 (76.4). cooled in an ice bath cooled in an ice bath to form a reaction mixture to evaporate The crude product was purified via flash silica column chromatography (2:1 hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Mercaptopropionic acid (0.69 mmol, 65 μL) was dissolved in 8 mL of water and cooled in an ice bath. This solution was added over 20-30 minutes to a solution of 5-methyl-1,4-naphthoquinone (0.69 mmole, 120 mg) dissolved in 15 mL of ethanol and cooled in an ice bath to form a reaction mixture. The reaction mixture was gradually allowed to warm to room temperature over a 1 hour period, and the ethanol was then allowed to evaporate. The crude product was purified via flash silica column chromatography (2:1 hexane:ethyl acetate with 1% v/v acetic acid) and provided a 70% yield of (5-methyl-1,4 naphthoquinonyl thio)- propionic acid, designated compound 1. 1H NMR data: (acetone-ds), δ 2.70 (s, 3H), 2.81 (t, J=7.2 Hz, 2H), 3.20 (t, J=7.2 Hz, 2H), 6.72 (s, 1H), 7.62 (d, J=7.5 Hz, 1H), 7.71 (t, J=7.5 Hz, 1H) 7.96 (d, J=Hz, 1H). LRMS m/z (rel. int.) 276 (M+, 30.5) 203 (100), 115 (68.2), 90 (41.0), 89 (76.4). cooled in an ice bath cooled in an ice bath to form a reaction mixture to evaporate The crude product was purified via flash silica column chromatography (2:1 hexane