Triethylamine → HCID 19887837, compound

HRID 654641Notes

Reaction equation

HRID 654641 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 successively 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 successively with NH4Cl (sat.), H2O, and brine
  2. customDrying
  3. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-12434e2e2f5e410794baffc0a9013b2e
Source dataset
uspto-grants-1992_07
Patent number
US05132420

Reaction notes

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