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

HRID 252803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 252803
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-42bd2cd077b54c73947b34af0983135f
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868205B2

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