反应详情

温度

-78 °C

Oxalyl chloride (0.46 mL, 5.25 mmol) was added dropwise to a solution of dimethyl sulfoxide (0.88 mL, 12.50 mmol) dissolved in dichloromethane (40 mL). The mixture was cooled to −78° C. and allowed to stir for 1 hour. A solution of (3-hydroxymethyl-2-methylphenoxy)acetic acid tert-butyl ester (1.26, 5.00 mmol) in dichloromethane was cannulated into the reaction mixture and allowed to stir at −78° C. for an additional hour. Triethylamine (3.49 mL, 25 mmol) was added. The reaction mixture was allowed to warm to room temperature, poured into water, and the layers were separated. The aqueous layer was extracted twice with dichloromethane. The combined organic extracts were washed with 2N hydrochloric acid and saturated sodium bicarbonate, dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification by silica gel chromatography, eluting with hexane/acetone, gave (3-formyl-2-methylphenoxy)acetic acid tert-butyl ester as a slightly yellow crystalline solid (1.07 g, 85.9%).

1. stirringto stir at −78° C. for an additional hour
2. temperatureto warm to room temperature
3. customthe layers were separated
4. extractionThe aqueous layer was extracted twice with dichloromethane
5. washThe combined organic extracts were washed with 2N hydrochloric acid and saturated sodium bicarbonate
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated in vacuo
8. customPurification by silica gel chromatography
9. washeluting with hexane/acetone