반응 #65685

반응 방정식

acetaldehyde

Magnesium

7-bromo-1,2,3,4-tetrahydro-1,4,4-trimethylquinoline

→

1,2,3,4-tetrahydro-α,1,4,4-tetramethyl-7-quinolinemethanol

수율 80.8%

용매

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타at 55°-60° C.
2. 2
   온도at reflux for an additional 2 hours
3. 3
   workup.ADDITIONthe mixture was poured on to ice/saturated ammonium chloride solution
4. 4
   추출extracted with ether
5. 5
   기타The oil obtained
6. 6
   기타after drying
7. 7
   기타evaporation of the solvent
8. 8
   여과was filtered over a silica gel column (eluting agent hexane/ethyl acetate 9:1)

실험 절차

2 g of Magnesium shavings were covered with 20 ml of tetrahydrofuran. A solution of 20.8 g of 7-bromo-1,2,3,4-tetrahydro-1,4,4-trimethylquinoline in 80 ml of tetrahydrofuran was added dropwise thereto at 55°-60° C. using an ultrasonics bath. Thereafter, the mixture was boiled at reflux for an additional 2 hours, cooled to 0° C. and a solution of 10 g of acetaldehyde in 80 ml of tetrahydrofuran was added dropwise thereto. After stirring at room temperature for 1 hour, the mixture was poured on to ice/saturated ammonium chloride solution and extracted with ether. The oil obtained after drying and evaporation of the solvent was filtered over a silica gel column (eluting agent hexane/ethyl acetate 9:1) and gave 14.5 g of 1,2,3,4-tetrahydro-α,1,4,4-tetramethyl-7-quinolinemethanol as a yellowish oil.

출처