Dimethyl Sulfoxide → 2-(Methoxymethoxy)-3-(7-methoxy-2-oxoquinoxalin-1(2H)-yl)propanal

Temperature

-78 °C

Oxalyl chloride (0.032 ml, 0.374 mmol) was dissolved in dichloromethane (2 ml). A solution of dimethyl sulfoxide (0.053 ml, 0.748 mmol) in dichloromethane (0.5 ml) was added to this solution at −78° C. and the mixture was stirred for 30 minutes. While maintaining the temperature at −78° C., a solution of 1-[3-hydroxy-2-(methoxymethoxy)propyl]-7-methoxyquinoxalin-2(1H)-one (100 mg, 0.340 mmol) in dichloromethane (3 ml) was further added and the mixture was stirred for 40 minutes. While maintaining the temperature at −78° C., triethylamine (0.261 ml, 1.870 mmol) was added and the mixture was stirred for 30 minutes. The temperature was raised to 0° C., the reaction solution was stirred for 2 hours, then diluted with dichloromethane and washed with water. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure to yield 109 mg (quantitative) of the title compound in the form of an orange oily product. The product was used as such for the next step without purification.

1. stirringthe mixture was stirred for 40 minutes
2. temperatureWhile maintaining the temperature at −78° C.
3. stirringthe mixture was stirred for 30 minutes
4. temperatureThe temperature was raised to 0° C.
5. stirringthe reaction solution was stirred for 2 hours
6. washwashed with water
7. dry with materialAfter drying over anhydrous sodium sulfate
8. customthe solvent was removed under reduced pressure

ORD record

ord-56999e63d5554c5b89b6ba4b68c02fff

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952010B2