반응 #529947

반응 방정식

DEAD

Intermediate 1

3-[1-(R)-(3-hydroxy-4-methoxyphenyl)-2-(4-pyridyl)ethyl]aniline

PPh3

2-indanol

2-indanol

PPh3

DEAD

→

title compound

수율 63.0%

(R)-4-[1-(3-(2-Indanyloxy)-4-methoxyphenyl)-2-(4-pyridyl)ethyl]aniline

수율 63.0%

용매

ethylacetate

THF

ethyl acetate

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred for an additional 1.5 h
2. 2
   기타then quenched by the addition of water (10 ml)
3. 3
   workup.ADDITIONThe mixture was diluted with ethyl acetate (100 ml)
4. 4
   세척washed with water (4×50 ml), brine (50 ml)
5. 5
   건조dried (MgSO4)
6. 6
   여과filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타to give a brown foam
9. 9
   추출extracted into hydrochloric acid (2×50 ml, 10% aq)
10. 10
    추출The aqueous extract
11. 11
    추출then extracted with ethyl acetate (2×100 ml)
12. 12
    세척The extract was washed with water (2×50 ml), brine (50 ml)
13. 13
    건조dried (MgSO4)
14. 14
    여과filtered
15. 15
    농축concentrated in vacuo
16. 16
    기타to give a white foam

실험 절차

To a solution of Intermediate 1 (1.0 g, 3.1 mmol) in THF (25 ml) at RT was added PPh3 (820 mg, 1 eq), 2-indanol (419 mg, 1 eq) and the solution stirred for 10 min prior to the addition of DEAD (492 μl, 1 eq). The reaction mixture was stirred at this temperature for 65 h before the further addition of 2-indanol (419 mg), PPh3 (820 mg) and DEAD (492 μl ). The mixture was stirred for an additional 1.5 h then quenched by the addition of water (10 ml). The mixture was diluted with ethyl acetate (100 ml), washed with water (4×50 ml), brine (50 ml), dried (MgSO4), filtered and concentrated in vacuo to give a brown foam. The crude product was redissolved in ethyl acetate (50 ml) and extracted into hydrochloric acid (2×50 ml, 10% aq). The aqueous extract was basified (NaOH to pH>10) then extracted with ethyl acetate (2×100 ml). The extract was washed with water (2×50 ml), brine (50 ml), dried (MgSO4), filtered and concentrated in vacuo to give a white foam. This was subjected to column chromatography (SiO2 ; ethylacetate) to afford the title compound (856 mg, 63%) as a white foam. δH (CDCl3) 3.05-3.35 (6H, m), 3.77 (3H, s), 4.06 (1H, t, J 8.0 Hz), 5.08 (1H, m), 6.52 (2H, d, J 7.8 Hz), 6.63 (1H, d, J 7.6 Hz), 6.70 (1H, s), 6.76 (2H, s), 6.95 (2H, d, J 6.0 Hz), 7.07 (1H, t, J 7.7 Hz), 7.18 (4H, m), and 8.41 (2H, d, J 5.9 Hz). m/z (ESI) 437 (MH+, 100%), 459 (MNa+, 2).

출처