Reaktion #43686

Reaktionsgleichung

iodine

ammonium chloride

4-methylbenzaldehyde

7-bromobenzo-[b]thiophene

magnesium

→

title compound

Ausbeute 57.0%

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

Ausbeute 57.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe mixture was extracted with diethyl ether
2. 2
   Waschenthe organic layer washed with brine
3. 3
   Trocknendried over anhydrous magnesium sulfate
4. 4
   SonstigeThe solvent was removed under reduced pressure
5. 5
   Sonstigethe residue was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran)
6. 6
   SonstigeFurther purification by column chromatography on silica gel (eluent; n-hexane/ethyl acetate=6/1)

Vorschrift

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.

Quelle