反応 #87947

反応方程式

Propargyl alcohol

lithium aluminium hydride

tri-n-butyl tin chloride

→

(Z)-3-tributylstannanyl-prop-2-en-1-ol

溶媒

THF

diethyl ether

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred for 3 hours
2. 2
   温度whilst gradually warming to room temperature
3. 3
   温度The reaction mixture was cooled to −5° C.
4. 4
   その他quenched by addition of water and 15% aqueous sodium hydroxide solution
5. 5
   温度then warmed to room temperature
6. 6
   workup.ADDITIONEthyl acetate was added
7. 7
   workup.STIRRINGthe mixture was stirred for 1 hour
8. 8
   ろ過The mixture was filtered through Celite
9. 9
   その他the filtrate was evaporated to dryness
10. 10
    その他The residue was purified by chromatography on a silica column which
11. 11
    洗浄had been pre-washed with 20% triethylamine in acetonitrile
12. 12
    洗浄The column was eluted with a mixture of ethyl acetate and pentane with a gradient of 0-10%

実験手順

Propargyl alcohol (5 mL) was added to a solution of lithium aluminium hydride (1M in THF, 43 mL) in THF (70 mL) at −78° C. The resultant mixture was warmed to room temperature and stirred for 18 hours. It was re-cooled to −78° C. and a solution of tri-n-butyl tin chloride (8.32 mL) in diethyl ether (50 mL) was added and the mixture was stirred for 3 hours whilst gradually warming to room temperature. The reaction mixture was cooled to −5° C. and quenched by addition of water and 15% aqueous sodium hydroxide solution then warmed to room temperature. Ethyl acetate was added and the mixture was stirred for 1 hour. The mixture was filtered through Celite and the filtrate was evaporated to dryness. The residue was purified by chromatography on a silica column which had been pre-washed with 20% triethylamine in acetonitrile. The column was eluted with a mixture of ethyl acetate and pentane with a gradient of 0-10% to give (Z)-3-tributylstannanyl-prop-2-en-1-ol (5.06 g) as a clear oil.

出典