تفاعل #167383

معادلة التفاعل

ethylacetate

acetone

Butyl Lithium

3-bromo-pyridine

→

2-(3-bromo-pyridin-4-yl)-propan-2-ol

المردود 41.8%

المذيبات

hexane

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe reaction mixture was stirred for a further 15 minutes at −90° C.
2. 2
   workup.STIRRINGwith stirring over a period of 1 hour
3. 3
   أخرىThe reaction mixture was quenched with aqueous NaHCO3 solution
4. 4
   استخلاصextracted with ethylacetate
5. 5
   تجفيفThe organic layer was dried over Na2SO4
6. 6
   تركيزconcentrated
7. 7
   أخرىPurification by column chromatography on silica gel (15% ethylacetate in hexane)

الإجراء التجريبي

Butyl Lithium (10.28 mL, 16.455 mmol) was added to a solution of DIPA (2.66 mL, 18.98 mmol) in THF (25 mL) at −78° C. The reaction mixture was stirred at −10° C. for 10 minutes, followed by the addition of 3-bromo-pyridine (500 mg, 2.212 mmol) in THF (10 mL) at −100° C. The reaction mixture was stirred for a further 15 minutes at −90° C. and was followed by the addition of acetone (1.675 mL, 22.78 mmol) in THF (10 mL) at −78° C. with stirring over a period of 1 hour. The reaction was monitored by TLC (5% ethylacetate in hexane). The reaction mixture was quenched with aqueous NaHCO3 solution and extracted with ethylacetate. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (15% ethylacetate in hexane) afforded 200 mg of 2-(3-bromo-pyridin-4-yl)-propan-2-ol (11% yield).

المصدر