반응 #1350560

반응 방정식

sodium borohydride

5-amino-2-methylphenol

2-thiophenecarboxaldehyde

sodium acetate

→

2-methyl-5-(thiophen-2-yl-methylamino)phenol

수율 32.5%

용매

methanol

반응 조건

후처리

1. 1
   workup.ADDITIONAfter the addition
2. 2
   workup.STIRRINGto stir for an additional 1.5 hours
3. 3
   workup.ADDITIONThe reaction mixture was poured
4. 4
   기타onto crushed ice slurry (200 g)
5. 5
   기타the resulting precipitate was collected
6. 6
   세척washed with cold water three times
7. 7
   기타air-dried

실험 절차

To a solution of 5-amino-2-methylphenol (12.30 g, 100 mmole) in methanol (100 mL) at 4° C. was added 2-thiophenecarboxaldehyde (16.82 g, 150 mmole) and sodium acetate (16.41 g, 200 mmole). The reaction mixture was stirred for 15 minutes and sodium borohydride (4.73 g, 125 mmole) was added portionwise over 1 hour at 4° C. After the addition was complete, the reaction was allowed to stir for an additional 1.5 hours. The reaction mixture was poured onto crushed ice slurry (200 g) and the resulting precipitate was collected, washed with cold water three times and air-dried to afford 2-methyl-5-(thiophen-2-yl-methylamino)phenol (7.12 g, 32% yield): mp 130.8-132.6° C.; 1HNMR (400 MHz, DMSO-d6) δ 1.94 (s, 3H), 4.34 (d, 2H, J=6.0 Hz), 5.91 (t, 1H, J=6.1 Hz), 6.00 (dd, 1H, J=2.3, 8.0 Hz), 6.11 (d, 1H, J=2.2 Hz), 6.70 (d, 1H, J=8.1 Hz), 6.95 (dd, 1H, J=3.5, 5.0 Hz), 7.00 (dd, 1H, J=0.8, 3.4 Hz), 7.34 (dd, 1H, J=1.0, 5.0 Hz), 8.79 (s, 1H); MS m/z 219 (M+).

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