Triphenylphosphine → Methyl Glycolate

After glycolic acid methyl ester (300 mg, 3.33 mmol), triphenylphosphine (1052 mg, 4.00 mmol), 1-methyl-5-mercapto-1H-tetrazole (465 mg, 4.00 mmol), and THF (12 ml) were added to a 50 ml flask, azodicarboxylic acid bis(2-methoxyethyl) ester (937 mg, 4.00 mmol) dissolved in THF (6 ml) was added dropwise thereto at 20° C., and the reaction was allowed to proceed for two hours. Water (0.5 mL) was added, and concentration was carried out. Then, water (10 ml) was added to the solution, and extraction was carried out using ethyl acetate (10 ml, ×2). Then, the organic layer was washed with water (10 mL) and saturated salt water (10 ml), and dehumidified with anhydrous magnesium sulfate. Subsequently, a crude product obtained by concentration was purified by column chromatography (silica gel, 70% ethyl acetate-hexane solution) to give acetic acid (1-methyl-1H-tetrazole-5-ylsulfanyl)methyl ester as a colorless oily substance (549 mg, yield: 88%/glycolic acid methyl ester).

1. additionwas added dropwise
2. customat 20° C.
3. concentrationconcentration
4. additionThen, water (10 ml) was added to the solution, and extraction
5. washThen, the organic layer was washed with water (10 mL) and saturated salt water (10 ml)
6. customSubsequently, a crude product obtained by concentration
7. customwas purified by column chromatography (silica gel, 70% ethyl acetate-hexane solution)

ORD-Eintrag

ord-eec2b1d236a949f88025e5d7d3244c63

Quelldatensatz

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07947816B2