반응 #465130

반응 방정식

3-benzoylpropionic acid

triethylamine

2-methyl-2-propanol

→

t-butyl 3-benzoylpropionate

수율 64.0%

용매

benzene

반응 조건

후처리

1. 1
   여과after which the THF solution was filtered
2. 2
   기타to remove the triethylamine hydrochloride
3. 3
   기타to yield a light beige solid
4. 4
   workup.STIRRINGthe mixture was stirred
5. 5
   온도with heating
6. 6
   workup.DISSOLUTIONto dissolve all of the solid
7. 7
   workup.ADDITIONwas added to the solution
8. 8
   workup.STIRRINGThe solution immediately turned dark red and was stirred at room temperature for 36 hours
9. 9
   세척The solution was washed with 10% aqueous HCl solution
10. 10
    건조The organic layer was then dried (MgSO4)
11. 11
    여과filtered
12. 12
    농축concentrated
13. 13
    기타The resultant oil was purified twice by column chromatography (silica gel, Eluent: 20% ethyl acetate: hexanes)
14. 14
    기타the resultant oil obtained
15. 15
    workup.DISTILLATIONwas distilled under reduced pressure

실험 절차

Once the 3-benzoylpropionic acid had dissolved, then 6.1 mL (0.0830 mol) of triethylamine was added. The solution was stirred for 6 hours, after which the THF solution was filtered to remove the triethylamine hydrochloride. The filtrate was rotoevaporated to yield a light beige solid. To this solid was added 200 mL of benzene followed by 6.0 mL (0.104 mol) of 2-methyl-2-propanol and the mixture was stirred with heating to dissolve all of the solid. After complete dissolution, 5.40 g (0.0442 mol) of DMAP was added to the solution. The solution immediately turned dark red and was stirred at room temperature for 36 hours. The solution was washed with 10% aqueous HCl solution, followed by 2×5% aq. NaOH solution and finally with water. The organic layer was then dried (MgSO4), filtered and concentrated. The resultant oil was purified twice by column chromatography (silica gel, Eluent: 20% ethyl acetate: hexanes) and the resultant oil obtained was distilled under reduced pressure to yield 6.45 g (64%) of t-butyl 3-benzoylpropionate as a colorless oil. lit bp 129-130° C. at 1.5 mm Hg.; 1HNMR ppm (δ), CDCL3 7.98 (d, 2H), 7.54 (m, 1H), 7.46 (m, 2H), 3.26 (t, 2H), 2.68 (t, 2H), 1.45 (s, 9H). 13CNMR ppm (δ), CDCl3, 198.3 (C=O), 172.1 (CO2), 136.7 (q), 133.0, 128.6, 128.0, 80.6 (C(CH3)3), 33.5, 29.4, 28.0 (CH3).

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