Triethylamine → HCID 19887837, compound

HRID 1494277Notes

Reaction equation

HRID 1494277 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([OH:14])[C:8]=3[O:7][C:6]=2[CH:15]=1.C(N(CC)CC)C.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].C(OCC)(=O)C>C1COCC1.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([O:14][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:8]=3[O:7][C:6]=2[CH:15]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 19887841HCID 19887841, compound

Product 1

HCID 19887837HCID 19887837, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-6-hydroxydibenzofuran (309 mg, 1.17 mmol) in 8 ml THF at room temperature were added triethylamine (0.23 ml, 1.6 mmol), 4-dimethylaminopyridine (14 mg, 0.12 mmol) and t-butyldimethylsilyl chloride (229 mg, 1.5 mmol). The mixture was stirred at room temperature overnight and then diluted into ethyl acetate and washed successfully with NH4Cl (sat.), H2O, and brine. Drying (MgSO4) and evaporation gave 421 mg of brown solid which was purified by flash chromatography through 40 g silica gel (10% EtOAc/hexane) to yield 388 mg (87%) of the title compound.

Workup

  1. washwashed successfully with NH4Cl (sat.), H2O, and brine
  2. customDrying
  3. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-00c5b050781e4db4b4bc4ccc408b8c85
Source dataset
uspto-grants-1991_06
Patent number
US05025008

Reaction notes

Loading…