反応 #66599

反応方程式

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

収率 52.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added drop-wise over 5 minutes
2. 2
   workup.STIRRINGAfter stirring for 1 hour the solution
3. 3
   温度was warmed to room temperature
4. 4
   その他quenched by the slow addition of 50 mL 10% NH4Cl
5. 5
   workup.ADDITIONAfter 100 mL of H2O was added the mixture
6. 6
   抽出was extracted with ethyl acetate
7. 7
   洗浄washed with H2O
8. 8
   洗浄washed with brine
9. 9
   乾燥The combined organics were dried over Na2SO4
10. 10
    ろ過filtered
11. 11
    濃縮concentrated in vacuo
12. 12
    その他to give an orange oil
13. 13
    その他Purification via flash chromatography (3:2 hexane/ethyl acetate)

実験手順

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.

出典