Ammonium Chloride → HCID 19095270, compound

2-(2-Bromoethyl)-1,3-dioxolane (4.5 ml) was added dropwise within 15 minutes under argon and while stirring at a maximum 30° C. to a suspension of Rieke magnesium, prepared from 5.1 g of magnesium chloride, in 150 ml of absolute tetrahydrofuran. The suspension was stirred at room temperature for 30 minutes, cooled to -70° C. and treated within 10 minutes with 6.1 g of N-methoxy-N-methyl-1,3-benzodioxol-5-carboxamide. The reaction mixture was stirred at -70° C. for 30 minutes and at room temperature for 2 hours and subsequently hydrolyzed with 100 ml of saturated ammonium chloride solution while cooling at a maximum 20° C. After the addition of 50 ml of water the mixture was extracted once with 150 ml of ethyl acetate and twice with 100 ml of ethyl acetate each time. The combined organic extracts were dried over MgSO4 and freed from solvent. The residue, 8.0 g of yellow oil, was chromatographed on 490 g of silica gel with ethyl acetate/hexane (1:5) as the eluent. 5.3 g (72%) of 1-(1,3-benzodioxol-5-yl)-3-(1,3-dioxol-2-yl)-1-propanone were isolated as a colourless solid. A sample crystallized colourless from a 20-fold amount of diethyl ether and melted at 94°-96° C.

1. temperaturecooled to -70° C.
2. temperaturewhile cooling at a maximum 20° C
3. extractionwas extracted once with 150 ml of ethyl acetate and twice with 100 ml of ethyl acetate each time
4. dry with materialThe combined organic extracts were dried over MgSO4
5. customThe residue, 8.0 g of yellow oil, was chromatographed on 490 g of silica gel with ethyl acetate/hexane (1:5) as the eluent

ORD record

ord-7ae7d278f1024e268d3e07302079e164

Source dataset

uspto-grants-1994_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05292732