반응 #168919

반응 방정식

dry ice

4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-benzaldehyde

2,2,6,6-tetramethyl piperidine

n-Butyllithium

2,4-Dimethoxypyrimidine

→

[4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-(2,4-dimethoxy-pyrimidin-5-yl)-methanol

수율 52.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added drop-wise over 5 minutes
2. 2
   workup.STIRRINGAfter stirring for 1 hour the solution
3. 3
   온도was warmed to room temperature
4. 4
   기타quenched by the slow addition of 50 mL 10% NH4Cl
5. 5
   workup.ADDITIONAfter 100 mL of H2O was added the mixture
6. 6
   추출was extracted with ethyl acetate
7. 7
   세척washed with H2O
8. 8
   세척washed with brine
9. 9
   건조The combined organics were dried over Na2SO4
10. 10
    여과filtered
11. 11
    농축concentrated in vacuo
12. 12
    기타to give an orange oil
13. 13
    기타Purification via flash chromatography (3:2 hexane/ethyl acetate)

실험 절차

Freshly distilled 2,2,6,6-tetramethyl piperidine (0.85 mL, 5.0 mmol) was dissolved in 20 mL THF and cooled to 0° C. n-Butyllithium (2.0 mL, 2.5 M in hexanes) was added drop-wise over 5 minutes and the mixture was allowed to stir for 30 minutes and then cooled to −78° C. 2,4-Dimethoxypyrimidine (0.353 g, 2.52 mmol) was added drop-wise over 5 min. After 45 min the solution was transferred via a dry ice cooled cannula to a solution of 4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-benzaldehyde (0.717 g, 2.52 mmol) in 20 mL THF at −78° C. After stirring for 1 hour the solution was warmed to room temperature and quenched by the slow addition of 50 mL 10% NH4Cl. After 100 mL of H2O was added the mixture was extracted with ethyl acetate, washed with H2O and washed with brine. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give an orange oil. Purification via flash chromatography (3:2 hexane/ethyl acetate) afforded [4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-(2,4-dimethoxy-pyrimidin-5-yl)-methanol (0.551 g, 52%) as a clear oil.

출처