Triethylamine → [(3-Bromonaphthalen-1-yl)methoxy](tert-butyl)dimethylsilane

HRID 1086872Notes

Reaction equation

HRID 1086872 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:12][O:13][Si:18]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 12749165(3-Bromonaphthalen-1-yl)methanol

Product 1

HCID 15166585[(3-Bromonaphthalen-1-yl)methoxy](tert-butyl)dimethylsilaneYield 98.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.49 g (6.3 mmoles) of 3-bromo-1-(hydroxymethyl)-naphthalene in 25 ml anhydrous CH2Cl2 were added sequentially N,N-dimethyl-4-aminopyridine (76.8 mg, 0.63 mmoles), t-butyldimethylchlorosilane (1.23 g, 8.2 mmoles) and triethylamine (1.22 ml, 8.8 mmoles). The resulting solution was stirred at room temperature for 2 hours under a N2 atmosphere and then partitioned between EtOAc and ice/H2O. The organic phase was separated, washed with brine, dried with anhydrous Na2SO4, filtered and concentrated under vacuum to provide a pale yellow liquid. The crude reaction residue was purified by column chromatography (44 g silica gel, packed and eluted with 9:1 hexanes:CH2Cl2) to provide 2.19 g of the title compound as a clear liquid.

Workup

  1. custompartitioned between EtOAc and ice/H2O
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto provide a pale yellow liquid
  8. customThe crude reaction residue
  9. customwas purified by column chromatography (44 g silica gel, packed and eluted with 9:1 hexanes:CH2Cl2)

Sources & evidence

ORD record
ord-d4f4a006556f48548b683aaeb8b65ff6
Source dataset
uspto-grants-1991_07
Patent number
US05032587

Reaction notes

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