2-Bromoethanol → (2-Bromoethoxy)-tert-butyldimethylsilane

HRID 2368927Notes

Reaction equation

HRID 2368927 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].[CH3:5][C:6]([Si:9](Cl)([CH3:11])[CH3:10])([CH3:8])[CH3:7]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][CH2:2][CH2:3][O:4][Si:9]([C:6]([CH3:8])([CH3:7])[CH3:5])([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 108982-BromoethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-bromo-ethanol (12.5 g, 0.1 mol) and TEA (11.2 g, 0.11 mol) in CH2Cl2 (40 mL), TBSCl (15.8 g, 0.105 mol) and DMAP (0.122 g, 1 mmol) were added. The reaction mixture was stirred at room temperature for 12 h, washed (10 mL 2M HCl, 10 mL H2O), dried (Na2SO4) and concentrated to give the desired product as colorless oil. 1H NMR (CDCl3): δ 3.88 (m, 2H), 3.39 (m, 2H), 0.89 (s, 9H), 0.08 (s, 6H).

Workup

  1. additionwere added
  2. washwashed (10 mL 2M HCl, 10 mL H2O)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7335454376af44e694e777a9148d1f37
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

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