Ethyl Acetate → Methyl 4-acetoxyindole-2-carboxylate

HRID 413791ノート

反応式

HRID 413791 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 22310858Methyl 4-acetoxyindole-2-carboxylate

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

反応条件

温度
25 °C

実験手順

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+).

後処理

  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%)

出典と根拠

ORDレコード
ord-66d863c9eea14e9c81cd4092cff6d8a1
出典データセット
uspto-grants-2003_05
特許番号
US06569888B1

反応ノート

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