반응 #1244254

ord-464a7899678d4d34b2c447cb9e864b86

반응 방정식

CNc1ccc(C=Cc2ccc(OCCOCCO)cc2)cc1
Compound 3a
CNc1ccc(C=Cc2ccc(OCCOCCO)cc2)cc1
2-(2-{4-[2-(4-Methylamino-phenyl)-vinyl]-phenoxy}-ethoxy)-ethanol
CC(C)(C)[Si](C)(C)Cl
TBDMSCl
c1c[nH]cn1
imidazole
CNc1ccc(C=Cc2ccc(OCCOCCO[Si](C)(C)C(C)(C)C)cc2)cc1
7a
수율 93.5%
CNc1ccc(C=Cc2ccc(OCCOCCO[Si](C)(C)C(C)(C)C)cc2)cc1
{4-[2-(4-{2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-ethoxy}-phenyl)-vinyl]-phenyl}-methyl-amine
수율 93.5%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타After standard workup with dichloromethane, the residue was purified by silica gel column chromatography (1.5% methanol in dichloromethane)

실험 절차

Compound 3a (45 mg, 0.14 mmol) and TBDMSCl (33 mg, 0.22 mmol) were dissolved in dichloromethane (10 ml) followed by imidazole (20 mg, 0.29 mmol). The solution was stirred at room temperature for 2 hours. After standard workup with dichloromethane, the residue was purified by silica gel column chromatography (1.5% methanol in dichloromethane) to afford 7a (56 mg, 91%): 1H NMR δ 7.40 (m, 4H), 6.90 (m, 4H), 6.75 (d, 2H, J=7.9 Hz), 4.15 (t, 2H), 3.88 (t, 2H), 3.82 (t, 2H), 3.66 (t, 2H), 2.85 (s, 3H), 0.92 (s, 9H), 0.09 (s, 6H).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07807135B2uspto-grants-2010_10