반응 #163474

반응 방정식

NaHCO3 Et2O

solution

N-(tert-butyl)-N-hexylideneamine

O-ethyl carbonisothiocyanatidate

NaHCO3

iodine

→

title compound

수율 67.7%

ethyl [(5Z)-4-butyl-2-tert-butylisothiazol-5(2H)-ylidene]carbamate

수율 67.7%

용매

THF

Et2O

pyridine

MeOH

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 2 hours
2. 2
   workup.STIRRINGstirred for 30 minutes
3. 3
   기타the organic layer was separated
4. 4
   추출The aqueous layer was extracted with Et2O (2×)
5. 5
   건조combined organics were dried (MgSO4)
6. 6
   농축concentrated in vacuo
7. 7
   workup.ADDITIONToluene and acetonitrile were added
8. 8
   기타evaporated
9. 9
   기타to remove water and pyridine
10. 10
    기타The crude compound was purified by flash chromatography

실험 절차

To a solution of Example 1A (4.2 g, 27 mmol) in THF (100 mL) at room temperature under N2 was added O-ethyl carbonisothiocyanatidate (3.55 g, 27 mmol). The reaction mixture was stirred for 1 hour and iodine (6.8 g, 27 mmol), MeOH (100 mL) and pyridine (10 mL) were added. The reaction mixture was stirred for 2 hours. The reaction mixture was poured into saturated NaHCO3/Et2O and stirred for 30 minutes. Additional saturated NaHCO3 and Et2O were added and the organic layer was separated. The aqueous layer was extracted with Et2O (2×) and combined organics were dried (MgSO4) and concentrated in vacuo. Toluene and acetonitrile were added and evaporated to remove water and pyridine. The crude compound was purified by flash chromatography using 0-100% EtOAc in hexane as eluent to give 5.2 g of the title compound as yellow solid. 1H NMR (300 MHz, CDCl3) δ ppm 0.93 (t, J=7.3 Hz, 3 H), 1.27-1.47 (m, 5 H), 1.54-1.73 (m, 11 H), 2.59-2.74 (m, 2 H), 4.28 (q, J=7.1 Hz, 2 H), 7.78 (s, 1 H). MS (DCI/NH3) m/z 285 (M+H)+.

출처