Reaction #57748

Reaction equation

methanol

4-(3-methoxy-propyl)-3-methyl-benzofuran-2-carboxylic acid

diisopropylaluminium hydride

sodium potassium tartrate

→

[4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]methanol

Yield 96.1%

Solvents

toluene

tetrahydrofuran

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Extractionthrice extracted with ethyl acetate
3. 3
   DryingCombined organic extracts were dried over sodium sulfate
4. 4
   Filtrationfiltered

Procedure

To 4-(3-methoxy-propyl)-3-methyl-benzofuran-2-carboxylic acid (0.2354 g, 0.853 mmol) in tetrahydrofuran (10 mL) cooled at 0° C. was added diisopropylaluminium hydride (3.41 mL, of a 1.0M solution in toluene) dropwise. After stirring for 1 hour methanol (5 mL) was added followed by saturated aqueous sodium potassium tartrate (5 mL). The resulting mixture was stirred for 15 minutes and was then thrice extracted with ethyl acetate. Combined organic extracts were dried over sodium sulfate, filtered, reduced to dryness and the resulting residue was subjected to silica gel gradient flash chromatography (hexanes/ ethyl acetate 10:1-3:1) which furnished 0.192 g (96%) of [4-(3-methoxypropyl)-3-methyl-1-benzofuran-2-yl]methanol as a white solid. MS (ES) m/z: 234.1 (M+).

Source