反応 #3781

反応方程式

Triphenylphosphine ethylbromide

sodium hydride dimethyl sulfoxide

4,6-dimethoxy-2-hydroxybenzaldehyde

→

3,5-dimethoxy-2-propylphenol

収率 46.4%

反応条件

後処理

1. 1
   その他at 50° C.
2. 2
   その他overnight
3. 3
   その他After the termination of the reaction
4. 4
   その他the resulting solution was partitioned with ethyl acetate and dilute hydrochloric acid
5. 5
   洗浄the resulting ethyl acetate phase was washed in water and subsequently in a saturated sodium chloride solution
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONto distill off the solvents under reduced pressure
8. 8
   その他The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=3:1)
9. 9
   workup.ADDITIONfollowed by addition of a catalytic amount of platinum dioxide for hydrogenation

実験手順

Triphenylphosphine ethylbromide (4.1 g) was added to a 2N sodium hydride/dimethyl sulfoxide solution (11 ml), prior to agitation at 50° C. for 30 minutes. To the mixture was added 4,6-dimethoxy-2-hydroxybenzaldehyde (1 g), for agitation at 50° C. overnight. After the termination of the reaction, the resulting solution was partitioned with ethyl acetate and dilute hydrochloric acid, and the resulting ethyl acetate phase was washed in water and subsequently in a saturated sodium chloride solution and dried over anhydrous magnesium sulfate, to distill off the solvents under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=3:1), followed by addition of a catalytic amount of platinum dioxide for hydrogenation, to recover 3,5-dimethoxy-2-propylphenol (0.5 g; yield of 46%). By 1H-NMR (90 MHz, CDCl3), the compound has the peaks shown below.

出典