반응 #1929085

반응 방정식

4-nitrobenzylbromide

Sodium hydride

tetramethyl methylenebisphosphonate

→

12

수율 30.0%

Tetramethyl 1-(4-nitrobenzyl)methylenebisphosphonate

수율 30.0%

용매

THF

DMF

반응 조건

후처리

1. 1
   기타The reaction was quenched by the addition of saturated aqueous NH4Cl (20 mL)
2. 2
   workup.ADDITIONAfter the addition of water (100 mL) the product
3. 3
   추출was extracted with EtOAc
4. 4
   세척the combined organics were washed with brine
5. 5
   건조dried over MgSO4
6. 6
   여과filtered
7. 7
   농축concentrated at reduced pressure
8. 8
   기타The crude product was purified by silica gel chromatography (0% to 10% MeOH in EtOAc)

실험 절차

Sodium hydride (1.02 g, 25.4 mmol) was added in portions to a stirring solution of tetramethyl methylenebisphosphonate in DMF (40 mL). After 30 min a solution of 4-nitrobenzylbromide (5.00 g, 23.1 mmol) in THF (5 mL) was added and the resulting mixture was stirred at room temperature for 4.5 hr. The reaction was quenched by the addition of saturated aqueous NH4Cl (20 mL). After the addition of water (100 mL) the product was extracted with EtOAc and the combined organics were washed with brine, dried over MgSO4, filtered and concentrated at reduced pressure. The crude product was purified by silica gel chromatography (0% to 10% MeOH in EtOAc) resulting in 12 as a colorless solid (2.55 g, 30%). 1H NMR (400 MHz, CDCl3) δ 2.65 (tt, J=6.5, 23.8, 1H), 3.31 (dt, J=6.5, 16.5, 2H), 3.73 (d, J=7.0, 6H), 3.75 (d, J=7.0, 6H), 7.42 (d, J=8.9, 2H), 8.15 (d, J=8.9, 2H).

출처