Diisobutylaluminum hydride → (1H-indol-2-yl)methanol

温度

-78 °C

In a 50-mL round-bottom flask, a total of 2.28 g (12 mmol) of ethyl 2-indolecarboxylate was dissolved in 15 mL of dry THF under N2. The solution was cooled to -78° C. (acetone-dry ice bath) and 24 mL (24 mmol) of 1.0M DIBAL in THF was added over a period of 1 h. The mixture was stirred for 2 h at -78° C., quenched with 10 mL of 1N HCl, then allowed to warm to room temperature. The reaction mixture was then extracted with ether (4×100 mL) and the ether layer was washed with 1N HCL (2×100 mL), dried over MgSO4, filtered, and evaporated in vacuo. The product was purified by flash chromatography (1:1 ethyl acetate:petroleum ether). Yield: 1.76 g (99%). 1H NMR (CDCl3): δ1.86 (t, 1H, J=6, OH), 4.82 (d, 2H, J=6), 6.40 (s, 1H), 7.0-7.3 (m, 2H), 7.34 (d, 1H, J=7.8), 7.58 (d, 1H, J=7.8), 8.36 (br s, 1H) MS (EI): m/z 147 (M+).

1. additionwas added over a period of 1 h
2. customquenched with 10 mL of 1N HCl
3. temperatureto warm to room temperature
4. extractionThe reaction mixture was then extracted with ether (4×100 mL)
5. washthe ether layer was washed with 1N HCL (2×100 mL)
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated in vacuo
9. customThe product was purified by flash chromatography (1:1 ethyl acetate:petroleum ether)

ORDレコード

ord-96f895a183034b818cda1ce120478271

出典データセット

uspto-grants-1996_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05523411