Reacción #172514

Ecuación de reacción

iodine

[3-benzyloxy-4-(2-thiophene-2-ylvinyl)phenyl]butyl[4-(tert-butyldiphenylsiloxy) butyl]amine

n-butyllithium

N,N-dimethylformamide

→

5-[2-[2-benzyloxy-4-[butyl[4-(tert-butyldiphenylsiloxy) butyl]amino]phenyl]vinyl]thiophene-2-carboaldehyde

Rendimiento 57.6%

Disolventes

ether

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.STIRRINGAfter the mixture was stirred for 1.5 hours
3. 3
   Otrothe bath was removed
4. 4
   workup.ADDITIONAt −10° C., 10 ml of water was added dropwise
5. 5
   workup.ADDITIONAfter the reaction mixture was poured into 100 ml of water, extraction with ethyl acetate
6. 6
   Lavadowashing with a saturated saline solution
7. 7
   Secadodrying over anhydrous sodium sulfate, and concentration
8. 8
   OtroThe residual liquid was purified by silica gel column chromatography
9. 9
   Otroto give a reddish orange oily matter
10. 10
    workup.STIRRINGAfter stirred at room temperature for 30 minutes
11. 11
    Lavadothe mixture was washed with a 5% sodium bisulfite solution
12. 12
    SecadoDrying over anhydrous magnesium sulfate and concentration
13. 13
    OtroThe residue was purified by silica gel column chromatography
14. 14
    Otroto give 1.21 g of a red oily matter (yield: 57.6%)

Procedimiento

In a stream of argon, in 20 ml of tetrahydrofuran was dissolved 2.02 g (3.0 mmol) of [3-benzyloxy-4-(2-thiophene-2-ylvinyl)phenyl]butyl[4-(tert-butyldiphenylsiloxy) butyl]amine, and 2.8 ml of n-butyllithium (1.6 mol solution in hexane) (4.48 mmol) was added dropwise thereto under cooling at −66 to −72° C. After the mixture was stirred for 35 minutes, 0.3 ml (3.9 mmol) of N,N-dimethylformamide was added dropwise thereto. After the mixture was stirred for 1.5 hours, the bath was removed and the temperature was allowed to rise. At −10° C., 10 ml of water was added dropwise. After the reaction mixture was poured into 100 ml of water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residual liquid was purified by silica gel column chromatography to give a reddish orange oily matter. Next, 1.43 g of the oily matter was dissolved in 150 ml of ether and 50 mg of iodine was added thereto. After stirred at room temperature for 30 minutes, the mixture was washed with a 5% sodium bisulfite solution and then with a saturated saline solution. Drying over anhydrous magnesium sulfate and concentration were performed. The residue was purified by silica gel column chromatography to give 1.21 g of a red oily matter (yield: 57.6%).

Fuente