5,6-Dihydroxyindole → Di(trimethylsilyloxy]indole

HRID 893548

Reaction equation

HRID 893548 reaction equation
[CH3:1]/[C:2](/[O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])=[N:3]\[Si](C)(C)C.O[C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1O)NC=C2>ClCCl>[CH3:10][Si:9]([CH3:12])([CH3:11])[O:8][C:1]1[C:21]2[C:22](=[CH:14][CH:15]=[CH:16][CH:20]=2)[NH:3][C:2]=1[O:8][Si:9]([CH3:10])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 1146835,6-DihydroxyindoleHCID 6913588N,O-bis(trimethylsilyl)acetamide

Product 1

HCID 131717434Di(trimethylsilyloxy]indoleYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 0.81 g (0.004 mole) of N,O-bis(trimethylsilyl) acetamide is added, stirring at room temperature, 0.3 g (0.002 mole) of 5,6-dihydroxy indole. When dissolution is completed, 2 ml dichloromethane are added and the solution is passed through a column of silica 60, eluating with dichloromethane. The first fraction obtained is concentrated in a rotavapor, then vacuum-dried. Thus are obtained 0.42 g (yield: 71%) of white crytal of 5,6[di(trimethylsilyloxy]indole.

Workup

  1. dissolutionWhen dissolution
  2. customThe first fraction obtained
  3. concentrationis concentrated in a rotavapor
  4. customvacuum-dried

Sources & evidence

ORD record
ord-4e923568dff24e089cee1cc2d5e733ab
Source dataset
uspto-grants-1992_06
Patent number
US05126125

Linked notes

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