반응 #57748

반응 방정식

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

수율 96.1%

용매

toluene

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   추출thrice extracted with ethyl acetate
3. 3
   건조Combined organic extracts were dried over sodium sulfate
4. 4
   여과filtered

실험 절차

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+).

출처