Imidazole → 3-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-1H-indole

HRID 2395090Notes

Reaction equation

HRID 2395090 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][CH:8]=[C:7]([CH2:10][CH2:11][OH:12])[C:5]=2[CH:6]=1.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C.C(OCC)(=O)C>[Si:18]([O:12][CH2:11][CH2:10][C:7]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[NH:9][CH:8]=1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 10685TryptopholHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 136339803-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-1H-indoleYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tryptophol (5.0 g, 31 mmol) in DMF (30 ml) was treated with imidazole (4.64 g, 68 mmol) and cooled to 0° C. tert-Butyldimethylsilyl chloride (5.14 g, 34.1 mmol) was added and the mixture was stirred at room temperature for 16 h. The mixture was then diluted with ethyl acetate (100 ml) and washed with water (2×100 ml) and the aqueous solutions were extracted with ethyl acetate (200 ml). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (30% ether/petroleum ether) yielded the title compound (8.43 g, 99% yield) as a colorless oil: IR (CCl4) 3910 (s), 3060 (w), 2960 (s), 2930 (s), 2850 (s), 1450 (m), 1370 (w), 1260 (s), 1100 (s), 900 (m), 840 (s), 780 (s), 750 (s) cm-1 ; 1H NMR (500 MHz, CDCl3) δ8.26 (br s, 1 H), 7.99 (d, J=7.8 Hz, 1 H), 7.64-7.50 (m, 4 H), 4.28 (t, J=7.3 Hz, 2 H), 3.38 (t, J=7.3 Hz, 2 H), 1.29 (s, 9 H), -0.43 (s, 6 H) ; 13C NMR (125 MHz, CDCl3) δ136.08, 127.62, 122.08, 121.75, 119.12, 118.79, 112.84, 111.04, 63.89, 28.98, 25.98, 18.34, -5.29; high resolution mass spectrum (Cl, NH3) m/z 276.1750 [(M+H)+ ; calcd for C16H25 NOSi: 276.1783].

Workup

  1. additionwas added
  2. washwashed with water (2×100 ml)
  3. extractionthe aqueous solutions were extracted with ethyl acetate (200 ml)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0c0ed5d381f4bb49f4f54f439e65a22
Source dataset
uspto-grants-1998_09
Patent number
US05811512

Reaction notes

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