反応 #43686

反応方程式

iodine

ammonium chloride

4-methylbenzaldehyde

7-bromobenzo-[b]thiophene

magnesium

→

title compound

収率 57.0%

Benzo[b]thiophen-7-yl-p-tolylmethanol

収率 57.0%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   抽出The mixture was extracted with diethyl ether
2. 2
   洗浄the organic layer washed with brine
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   その他The solvent was removed under reduced pressure
5. 5
   その他the residue was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran)
6. 6
   その他Further purification by column chromatography on silica gel (eluent; n-hexane/ethyl acetate=6/1)

実験手順

A Grignard reagent was prepared using 7-bromobenzo-[b]thiophene (1.0 g), magnesium (0.13 g), a catalytic amount of iodine and tetrahydrofuran (3 mL) according to the general method. To the Grignard reagent solution was added a solution of 4-methylbenzaldehyde (0.62 g) in tetrahydrofuran (5 mL) at 0° C. under an argon atmosphere. The reaction mixture was stirred at room temperature overnight and a saturated ammonium chloride aqueous solution was added to the mixture. The mixture was extracted with diethyl ether, and the organic layer washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran). Further purification by column chromatography on silica gel (eluent; n-hexane/ethyl acetate=6/1) gave the title compound (0.68 g) as yellow oil.

出典