تفاعل #86290

معادلة التفاعل

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

2-(methyldithio)isobutyraldehyde

sodium borohydride

→

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

المردود 65.0%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   workup.DISSOLUTIONuntil completely dissolved (3 hours)
2. 2
   أخرىwas then quenched slowly with cold 5% HCl solution
3. 3
   workup.ADDITIONThe mixture was diluted with dichloromethane
4. 4
   استخلاصthen extracted with dichloromethane
5. 5
   غسيلwashed with brine
6. 6
   تجفيفThe organic extracts were dried over anhydrous sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىPurification by silica gel chromatography (MeOH/DCM)

الإجراء التجريبي

(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.

المصدر