반응 #671281

반응 방정식

EtMgBr

1a

5-phenyldipyrromethane

6a

S-2-Pyridyl 4-methylbenzothioate

→

solid

수율 98.9%

S-2-Pyridyl 4-bromobenzothioate

수율 98.9%

용매

THF

THF

반응 조건

후처리

1. 1
   온도cooled to −78° C
2. 2
   workup.STIRRINGThe mixture was stirred for 10 min at −78° C
3. 3
   기타Then the cooling bath was removed
4. 4
   workup.STIRRINGthe mixture was stirred for 20 min
5. 5
   기타the reaction was quenched with saturated aqueous NH4Cl (150 mL)
6. 6
   workup.ADDITIONThe mixture was diluted with THF (10 mL)
7. 7
   세척washed with water (100 mL)
8. 8
   건조dried (Na2SO4)
9. 9
   기타Removal of solvents and chromatography [silica (6×24 cm), CH2Cl2 (2300 mL)]

실험 절차

Exemplified for 1-(4-Methylbenzoyl)-5-phenyldipyrromethane (2a). A solution of EtMgBr (50.0 mL, 50.0 mmol, 1.0 M in THF) was added via syringe to a stirred solution of 1a (4.44 g, 20.0 mmol) in THF (20 mL) under argon. The mixture was stirred for 10 min at room temperature and then cooled to −78° C. A solution of 6a (4.58 g, 20.0 mmol) in THF (20 mL) was added. The mixture was stirred for 10 min at −78° C. Then the cooling bath was removed, the mixture was stirred for 20 min, and then the reaction was quenched with saturated aqueous NH4Cl (150 mL). The mixture was diluted with THF (10 mL), washed with water (100 mL), and then dried (Na2SO4). Removal of solvents and chromatography [silica (6×24 cm), CH2Cl2 (2300 mL)] afforded a golden amorphous solid (5.82 g, 86%): mp 69-70° C.; 1H NMR δ 2.43 (s, 3H), 5.55 (s, 1H), 5.95-6.01 (m, 1H), 6.05-6.09 (m, 1H), 6.14-6.18 (m, 1H), 6.67-6.71 (m, 1H), 6.79-6.82 (m, 1H), 7.20-7.35 (m, 7H), 7.72-7.76 (m, 2H), 8.05-8.22 (brs, 1H), 9.50-9.68 (brs, 1H); Anal. Calcd for C23H20N2O: C, 81.15; H, 5.92; N, 8.23. Found: C, 80.74; H, 5.74; N, 8.25.

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