Triethylamine → HCID 10546047, compound

HRID 2226777Notes

Reaction equation

HRID 2226777 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].C(N(CC)CC)C>C(Cl)Cl>[Si:14]([O:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 106576502-(5-Bromo-1H-indol-1-yl)ethanol

Product 1

HCID 10546047HCID 10546047, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1(2-hydroxyethyl)-5-bromoindole (6 gm, 0.025 mol), t-butyldimethylsilyl chloride (4.5 gm, 0.03 mol) and triethylamine (4.2 ml, 0.03 mol) in CH2Cl2 (60 ml) was stirred for 12 hours at room temperature. The reaction mixture was then washed twice with H2O, dried over Na2SO4, filtered and concentrated in vacuo to provide the title compound as a yellow oil. 1H NMR was consistent with the desired structure.

Workup

  1. washThe reaction mixture was then washed twice with H2O
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8cadb0c6be94c9d8e497ae38d8c4f88
Source dataset
uspto-grants-1994_09
Patent number
US05349061

Reaction notes

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