Ethyl Acetate → Methyl 4-acetoxyindole-2-carboxylate

HRID 413791노트

반응식

HRID 413791 반응식
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:18]([O:20][CH3:21])=[O:19])[NH:13]2)[C:2]1C=CC=CC=1.C(OCC)(=[O:24])C>[Pd]>[C:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:18]([O:20][CH3:21])=[O:19])[NH:13]2)(=[O:24])[CH3:2]

참가 물질

4

반응물 2

HCID 8857Ethyl AcetateHCID 4777865methyl 4-(benzyloxy)-1H-indole-2-carboxylate

생성물 1

HCID 22310858Methyl 4-acetoxyindole-2-carboxylate

시약·촉매·용매 1

HCID 23938Palladium촉매

반응 조건

온도
25 °C

실험 절차

A solution of methyl 4-benzyloxyindole-2-carboxylate (48 g) in ethyl acetate (1 litre) at 50-60° C. was hydrogenated over 5%Pd-C catalyst (4.0 g) at 1 atmosphere pressure for 6 hours, until 3.7 litres of hydrogen was absorbed. The catalyst was filtered off and washed with warm ethyl acetate(100 ml). To the combined filtrates was added acetic anhydride (40 ml) and 4-dimethylaminopyridine (1.0 g), and the solution was stirred for 1 hour at 25° C. Ethanol (15 ml) was added and the solution reduced to halt volume by evaporation in vacuo, then hexane (1 litre) was added to cause crystallisation of the product as white needles (37 g, 93%). NMR d (CD3SOCD3) 2.34 (s, 3H), 3.85 (s, 3H), 6.80 (d, 1H), 7.06 (s, 1H), 7.23 (t, 1H), 7.29-7.35 (m, 1H), 12.1 (bs, 1H); M/z (−) 232 (M-H+).

후처리

  1. customat 50-60° C.
  2. customfor 6 hours
  3. customuntil 3.7 litres of hydrogen was absorbed
  4. filtrationThe catalyst was filtered off
  5. washwashed with warm ethyl acetate(100 ml)
  6. additionTo the combined filtrates was added acetic anhydride (40 ml) and 4-dimethylaminopyridine (1.0 g)
  7. additionEthanol (15 ml) was added
  8. customby evaporation in vacuo
  9. additionhexane (1 litre) was added
  10. customcrystallisation of the product as white needles (37 g, 93%)

출처 및 근거

ORD 기록
ord-66d863c9eea14e9c81cd4092cff6d8a1
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06569888B1

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