3,4,5-Trimethoxybenzaldehyde → Methyl 1-(3,4,5-Trimethoxy-benzyl)-2,3-dihydro-1H-indole-5-carboxylate

HRID 252803ノート

反応式

HRID 252803 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[CH:19]=O.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[CH3:27][O:26][C:22]1[CH:21]=[C:18]([CH:17]=[C:16]([O:15][CH3:14])[C:23]=1[O:24][CH3:25])[CH2:19][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 12688Dibutyltin dichlorideHCID 12752Phenylsilane2 回HCID 21782110methyl 2,3-dihydro-1H-indole-5-carboxylate

生成物 1

HCID 58930491Methyl 1-(3,4,5-Trimethoxy-benzyl)-2,3-dihydro-1H-indole-5-carboxylate収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 20 (300 mg, 1.69 mmol), 3,4,5-trimethoxybenzaldehyde (365 mg, 1.86 mmol) and dibutyltin dichloride (51 mg, 0.17 mmol) in THF (8 mL) was added phenylsilane (229 μl, 1.86 mmol). The mixture was stirred overnight at room temperature under nitrogen. Additional aldehyde and phenylsilane were added and the stirring continued until starting material was consumed. THF was evaporated in vacuum and the residue was purified by flash chromatography (eluent 20% EtOAc in hexane). The compound was further purified by re-crystallization in a mixture EtOAc/hexane and finally by a second flash chromatography (eluent 20% EtOAc in hexane) to give the title compound 21 (428 mg, 71%) as a white solid. 1H-NMR (DMSO) δ: 2.96 (t, J=8.4 Hz, 2H); 3.45 (t, J=8.7 Hz, 2H); 3.61 (s, 3H); 3.71 (s, 6H); 3.72 (s, 3H); 4.30 (s, 2H); 6.59 (s, 2H); 6.61 (d, J=8.4 Hz, 1H), 7.54 (d, J=1.6 Hz, 1H); 7.63 (dd, J=1.8, 8.4 Hz, 1H).

後処理

  1. customwas consumed
  2. customTHF was evaporated in vacuum
  3. customthe residue was purified by flash chromatography (eluent 20% EtOAc in hexane)
  4. customThe compound was further purified by re-crystallization in a mixture EtOAc/hexane and finally by a second flash chromatography (eluent 20% EtOAc in hexane)

出典と根拠

ORDレコード
ord-42bd2cd077b54c73947b34af0983135f
出典データセット
uspto-grants-2011_01
特許番号
US07868205B2

反応ノート

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