تفاعل #168919

معادلة التفاعل

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

المردود 52.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added drop-wise over 5 minutes
2. 2
   workup.STIRRINGAfter stirring for 1 hour the solution
3. 3
   درجة الحرارةwas warmed to room temperature
4. 4
   أخرىquenched by the slow addition of 50 mL 10% NH4Cl
5. 5
   workup.ADDITIONAfter 100 mL of H2O was added the mixture
6. 6
   استخلاصwas extracted with ethyl acetate
7. 7
   غسيلwashed with H2O
8. 8
   غسيلwashed with brine
9. 9
   تجفيفThe combined organics were dried over Na2SO4
10. 10
    ترشيحfiltered
11. 11
    تركيزconcentrated in vacuo
12. 12
    أخرىto give an orange oil
13. 13
    أخرىPurification via flash chromatography (3:2 hexane/ethyl acetate)

الإجراء التجريبي

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.

المصدر