Dimethylformamide → tert-Butyl (5-vinylthiazol-2-yl)carbamate

반응식

[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[S:9][C:10](Br)=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].CN(C=O)C.[CH2:22]1COC[CH2:23]1>>[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]1[S:9][C:10]([CH:22]=[CH2:23])=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

반응물 4

HCID 6228Dimethylformamide

HCID 8028Tetrahydrofuran2회

HCID 433294Lithium Chloride

HCID 21300388tert-butyl N-(5-bromo-1,3-thiazol-2-yl)carbamate

생성물 1

HCID 53486835tert-Butyl (5-vinylthiazol-2-yl)carbamate

실험 절차

(5-Bromo-thiazol-2-yl)-carbamic acid tert-butyl ester (0.200 g, 0.71 mmol), tetrakis(triphenylphospine)palladium (0.042 g, 0.036 mmol), lithium chloride (0.91 g, 2.14 mmol), and tributyl (vinyl)stannate (0.68 g, 2.14 mmol) were taken in 8 mL of THF and 8 mL of DMF and reflux for 2 hrs. After completion of reaction THF was removed under reduced pressure on ratavapour and the residue was partioned between ethyl acetate (20 mL) and water (20 mL). The layers were separated. Aq. Layer was extracted with ethyl acetate (2×20 mL). The combined organic layer was washed with brine and dried over anhydrous sodium sulfate filtered and concentrated under reduced pressure to get the crude product which was purified by preparative TLC to get the pure product (5-Vinyl-thiazol-2-yl)-carbamic acid tert-butyl ester (0.137 g).