Ethyl orthoformate → 1-diethoxymethyl-1H-indole-3-carbonitrile

HRID 1362350Notes

Reaction equation

HRID 1362350 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]#[N:11])=[CH:2]1.[CH2:12]([O:14][CH:15](OCC)[O:16][CH2:17][CH3:18])[CH3:13]>>[CH2:12]([O:14][CH:15]([O:16][CH2:17][CH3:18])[N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]#[N:11])=[CH:2]1)[CH3:13]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 2302823-Cyanoindole

Product 1

HCID 592776081-diethoxymethyl-1H-indole-3-carbonitrileYield 86%

Procedure

1H-Indole-3-carbonitrile (5.07 g, 35.7 mmol) was heated with triethylorthoformate (60 mL) in a pressure vessel at 160° C. for 3 d. Upon cooling, the solvent was evaporated and the residue was submitted to chromatography (20% ether in hexanes) to afford the title compound (7.46 g, 86%). NMR (300 MHz, CDCl3, δ): 7.92 (s, 1H), 7.76 (m, 1H), 7.62 (m, 1H), 7.32 (m, 2H), 6.23 (s, 1H), 3.63 (m, 4H), 1.23 (t, J=7.2 Hz, 6H).

Workup

  1. temperatureUpon cooling
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-3fd52958fad949728108069044b0cffb
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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