تفاعل #167753

معادلة التفاعل

diethanolamine

tert-butyl 4-acetylbenzoate

tetrahydrofuran

(−)-B-chlorodiisopinocampheylborane

→

title compound

المردود 103.3%

tert-butyl 4-[(1S)-1-hydroxyethyl]benzoate

المردود 103.3%

المذيبات

hexane

ظروف التفاعل

المعالجة

1. 1
   تركيزThe reaction solution was concentrated
2. 2
   workup.ADDITIONthe residue was diluted by diethyl ether
3. 3
   أخرىTo the thus solution obtained
4. 4
   workup.STIRRINGthe mixture was stirred at room temperature for 2 hours
5. 5
   أخرىThe precipitates were removed by filtration
6. 6
   تركيزthe filtrate was concentrated
7. 7
   أخرىThe residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=9/1 to 4/1)

الإجراء التجريبي

To tert-butyl 4-acetylbenzoate (3.33 g) in a tetrahydrofuran (23 ml) solution, (−)-B-chlorodiisopinocampheylborane in a 65% hexane solution (11.2 ml) was added dropwise under ice cooling, then the mixture was stirred at that temperature for 1.5 hours. The reaction solution was concentrated, and the residue was diluted by diethyl ether. To the thus solution obtained, diethanolamine (4.3 ml) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours. The precipitates were removed by filtration, and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, hexane/ethyl acetate=9/1 to 4/1) to obtain the title compound (3.47 g).

المصدر