반응 #1276199

반응 방정식

lithium borohydride

ethyl {2-[7-(1-methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate

tetrahydrofuran

methanol

→

title compound

수율 46.0%

2-[(7-(1-Methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}ethanol

수율 46.0%

용매

Water

반응 조건

후처리

1. 1
   추출the mixture was extracted with ethyl acetate
2. 2
   세척The organic layer was washed with brine
3. 3
   건조dried (MgSO4)
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:2 to 9:1, volume ratio)
7. 7
   기타to give a pale yellow amorphous solid
8. 8
   기타The solid was crystallized from ethyl acetate-diethyl ether

실험 절차

To a mixture of ethyl {2-[7-(1-methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (500 mg), tetrahydrofuran (20 mL) and methanol (5 mL) was added lithium borohydride (110 mg) at 0° C. The whole was stirred at room temperature for 2 h. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:2 to 9:1, volume ratio) to give a pale yellow amorphous solid. The solid was crystallized from ethyl acetate-diethyl ether to give the title compound (210 mg, 46%) as pale yellow crystals. The crystals were recrystallized from ethyl acetate-diethyl ether to give pale yellow prisms. MS 476 (MH+). mp 172-173° C.

출처