반응 #87947

반응 방정식

Propargyl alcohol

lithium aluminium hydride

tri-n-butyl tin chloride

→

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

용매

THF

diethyl ether

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred for 3 hours
2. 2
   온도whilst gradually warming to room temperature
3. 3
   온도The reaction mixture was cooled to −5° C.
4. 4
   기타quenched by addition of water and 15% aqueous sodium hydroxide solution
5. 5
   온도then warmed to room temperature
6. 6
   workup.ADDITIONEthyl acetate was added
7. 7
   workup.STIRRINGthe mixture was stirred for 1 hour
8. 8
   여과The mixture was filtered through Celite
9. 9
   기타the filtrate was evaporated to dryness
10. 10
    기타The residue was purified by chromatography on a silica column which
11. 11
    세척had been pre-washed with 20% triethylamine in acetonitrile
12. 12
    세척The column was eluted with a mixture of ethyl acetate and pentane with a gradient of 0-10%

실험 절차

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.

출처