Dimethylformamide → HCID 19102630, compound

Temperature

-78 °C

n-Butyllithium (18.6 ml of a 2.5M solution in hexane, 46.5 mmol) and N,N,N',N'-tetramethylethylenediamine (5.38 g, 46.3 mmol), respectively, were added (using a syringe) to a stirred solution of 5-(1-ethoxyethoxy)-1,3-benzodioxole (8.9 g, 42.4 mmol) in dry THF (100 ml) in a nitrogen atmosphere at -78° C. The resulting solution was allowed to attain room temperature and then cooled to -78° C. A solution of N,N-dimethylformamide (3.70 g, 50.6 mmol) in dry THF (20 ml) was added using a syringe, and the reaction mixture was allowed to attain room temperature. The resulting mixture was quenched with water and extracted with diethyl ether (3times). The combined ether layers were washed with water (2 times), dried over Na2SO4, filtered and evaporated in vacuo to to yield 5-(1-ethoxyethoxy)-4-formyl-1,3-benzodioxole (9.7 g, 96% yield; compound No. 2) as a pale yellow solid, m.p. 48°- 50° C.

1. customto attain room temperature
2. customto attain room temperature
3. customThe resulting mixture was quenched with water
4. extractionextracted with diethyl ether (3times)
5. washThe combined ether layers were washed with water (2 times)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated in vacuo

ORD record

ord-1a1aa75267c34654bd72a6772479a5de

Source dataset

uspto-grants-1994_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05281595