반응 #86290

반응 방정식

(5-amino-1,3-phenylene)dimethanol

2-(methyldithio)isobutyraldehyde

sodium borohydride

→

(5-(2-methyl-2-(methyldisulfanyl)propylamino)-1,3-phenylene)dimethanol

수율 65.0%

용매

ethanol

반응 조건

후처리

1. 1
   workup.DISSOLUTIONuntil completely dissolved (3 hours)
2. 2
   기타was then quenched slowly with cold 5% HCl solution
3. 3
   workup.ADDITIONThe mixture was diluted with dichloromethane
4. 4
   추출then extracted with dichloromethane
5. 5
   세척washed with brine
6. 6
   건조The organic extracts were dried over anhydrous sodium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated under reduced pressure
9. 9
   기타Purification by silica gel chromatography (MeOH/DCM)

실험 절차

(5-amino-1,3-phenylene)dimethanol (2.5 g, 16.32 mmol) and 2-(methyldithio)isobutyraldehyde (2.347 ml, 16.32 mmol) were stirred at ambient temperature in absolute ethanol (82 ml) until completely dissolved (3 hours). The mixture was cooled to 0° C. in an ice bath and sodium borohydride (0.741 g, 19.59 mmol) was added. The reaction was stirred for 1 hour at 0° C., and was then quenched slowly with cold 5% HCl solution. The mixture was diluted with dichloromethane and the pH was adjusted to pH=8 with saturated sodium bicarbonate solution then extracted with dichloromethane and then washed with brine. The organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography (MeOH/DCM) yielded (5-(2-methyl-2-(methyldisulfanyl)propylamino)-1,3-phenylene)dimethanol (3g, 65%) as a white solid. 1H NMR (400 Hz, CDCl3): δ6.62 (s, 1H), 6.54 (s, 2H), 4.53 (s, 4H), 3.13 (s, 2H), 2.30 (s, 3H), 1.32 (s, 6H). See FIG. 47.

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