反応 #163474

反応方程式

NaHCO3 Et2O

solution

N-(tert-butyl)-N-hexylideneamine

O-ethyl carbonisothiocyanatidate

NaHCO3

iodine

→

title compound

収率 67.7%

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

収率 67.7%

溶媒

THF

Et2O

pyridine

MeOH

反応条件

後処理

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 2 hours
2. 2
   workup.STIRRINGstirred for 30 minutes
3. 3
   その他the organic layer was separated
4. 4
   抽出The aqueous layer was extracted with Et2O (2×)
5. 5
   乾燥combined organics were dried (MgSO4)
6. 6
   濃縮concentrated in vacuo
7. 7
   workup.ADDITIONToluene and acetonitrile were added
8. 8
   その他evaporated
9. 9
   その他to remove water and pyridine
10. 10
    その他The crude compound was purified by flash chromatography

実験手順

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)+.

出典