Iodoethane → HCID 53924449, compound

NaH (60% suspension in mineral oil, 15.6 g, 0.39 mole) was washed with and suspended in ether (300 mL). To this suspension, ethyl formate (29.1 mL, 0.36 mole, 1.2 eq) was added and the mixture was cooled in an ice bath. Ethyl fluoroacetate (29.0 mL, 0.3 mole) was added slowly over 1 hour. After 2 hours the ice bath was removed and the reaction was stirred for another hour. After evaporation of the solvent, the residue was redissolved in 350 mL of dry DMF and cooled in an ice bath, and ethyl iodide (48 mL, 0.6 mole) was added dropwise. The solution was allowed to warm to room temperature and stirred overnight, then quenched with saturated aqueous solution of NH4Cl (100 mL). The mixture was diluted with ether and extracted with water. The separated ether layer was washed with sodium thiosulfate, brine and dried over MgSO4. After concentration under vacuum, the residue was distilled to give ethyl 3-ethoxy-2-fluoroacrylate (12, R9 =ethyl, 73°-85° C./14 mmHg) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ1.35 (t, 3H), 1.39 (t, 3H), 4.10 (q, 2H), 4.30 (q, 2H), 6.95 (d, 1H).

1. temperaturethe mixture was cooled in an ice bath
2. customAfter 2 hours the ice bath was removed
3. customAfter evaporation of the solvent
4. dissolutionthe residue was redissolved in 350 mL of dry DMF
5. temperaturecooled in an ice bath
6. stirringstirred overnight
7. customquenched with saturated aqueous solution of NH4Cl (100 mL)
8. additionThe mixture was diluted with ether
9. extractionextracted with water
10. washThe separated ether layer was washed with sodium thiosulfate, brine
11. dry with materialdried over MgSO4
12. concentrationAfter concentration under vacuum
13. distillationthe residue was distilled

ORD record

ord-899c74c426ee4f16bb5df7b0e38e83c3

Source dataset

uspto-grants-1997_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05693813