Triethylamine → HCID 10546047, compound

HRID 1656273Notes

Reaction equation

HRID 1656273 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-684b3c1d80134232bdb85ae9e5ec500e
Source dataset
uspto-grants-1993_10
Patent number
US05252732

Reaction notes

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