Hydrochloric Acid → HCID 86698278, Verbindung

Temperatur

65 °C

To a suspension of sodium selenide (5.35 g, 42.49 mmol) in DMF (43 mL) was added a solution of methyl 3-chloro-4,4-dimethylpent-2-enoate (7.5 g, 42.49 mmol) in DMF (10 mL) at rt for 5 min and stirred the mixture at 60-70° C. for 2 h. Then chloroacetonitrile (2.785 mL, 42.49 mmol) was added dropwise to the reaction mixture and again stirred at 60-70° C. for 2 h. Then, a solution of sodium methoxide (2.29 g, 42.49 mmol) in dry methanol (26 mL) was added dropwise and stirring was continued for 1 h at the same temperature. The reaction mixture was poured into ice cold water and acidified with dil. HCl. The solution was extracted with chloroform (3×200 mL) and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The residue was chromatographed over silica gel column using hexane-EtoAc (80:20) as eluents to give the product as a red color oil (7.5 g, 77%). 1H NMR (400 MHz, CDCl3): δ 6.76 (1H, s), 1.35 (9H, s); LC-MS (negative ion mode): m/z 226, 228 (M−H)−.

1. stirringagain stirred at 60-70° C. for 2 h
2. stirringstirring
3. waitwas continued for 1 h at the same temperature
4. additionThe reaction mixture was poured into ice cold water
5. extractionThe solution was extracted with chloroform (3×200 mL)
6. washthe combined chloroform layer was washed with water, brine
7. dry with materialdried over sodium sulfate
8. filtrationThe solution was filtered
9. customevaporated the solvent
10. customThe residue was chromatographed over silica gel column

ORD-Eintrag

ord-f852013aefa04a059ad143ebe0dcea03

Quelldatensatz

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08815879B2