Dichloromethane → 5-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde

HRID 10681Notes

Reaction equation

HRID 10681 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:22]=[C:21]([CH:23]=[O:24])[C:20]([O:25][CH3:26])=[CH:19][C:18]=1[O:27][CH3:28])=O)(C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].C(Cl)Cl>C1COCC1>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[C:18]([O:27][CH3:28])=[CH:19][C:20]([O:25][CH3:26])=[C:21]([CH:22]=1)[CH:23]=[O:24]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724141Tetrabutylammonium Fluoride2×HCID 161163072-(5-Formyl-2,4-dimethoxyphenyl)indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 161156215-(1H-indol-2-yl)-2,4-dimethoxybenzaldehydeYield 30.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ex-61A: 2-(5-Formyl-2,4-dimethoxy-phenyl)-indole-1-carboxylic acid tert-butyl ester (Ex-36A, 2.0 g, 5.2 mmol) was dissolved in 100 ml of THF, and Bu4NF (6.86 g, 26 mmol) was added. The reaction mixture was stirred at room temperature overnight. No reaction occured at this condition. Then, Bu4NF (6.86 g, 26 mmol) was added to the mixture, and the mixture was stirred at reflux for 4 days. The reaction was about 50% completion (HPLC). The reaction mixture was poured into CH2Cl2, and washed with water and brine. The organic phase was dried over MgSO4, and concentrated. The residue was purified by column chromatography (EtOAc: Hex, 2:1) to give 0.45 g (30%) of 5-(1H-indol-2-yl)-2,4-dimethoxy-benzaldehyde. 1H-NMR (CDCl3) δ 10.37 (s, 1H), 9.25 (br, 1H), 8.28 (s, 1H), 7.63 (d, J=8 Hz, 1H), 7.39 (d, J=8 Hz, 1H), 7.08–7.20 (m, 2H), 6.92 (d, J=2 Hz, 1H), 6.56 (s, 1H) 4.11 (s, 3H), 4.00 (s, 3H). HMRS (EI) calcd. for C17H15NO3: 281.1052; found: 281.1049.

Workup

  1. stirringthe mixture was stirred
  2. temperatureat reflux for 4 days
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (EtOAc: Hex, 2:1)

Sources & evidence

ORD record
ord-9e936e358d2f4910be2c07fb3e247bb1
Source dataset
uspto-grants-2006_08
Patent number
US07094801B2

Reaction notes

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