Triethylamine → 1-(2-((Tert-butyldimethylsilyl)oxy)ethyl)azocane

HRID 2368906Notes

Reaction equation

HRID 2368906 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:17][CH2:18][O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl>[Si:20]([O:19][CH2:18][CH2:17][N:1]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14276AzocanHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 866828951-(2-((Tert-butyldimethylsilyl)oxy)ethyl)azocaneYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of azocane (5.59 g, 49.4 mmol) and triethylamine (6.53 g, 64.7 mmol) in DCM (50 mL) at room temperature was added (2-bromoethoxy)(tert-butyl)dimethylsilane (13.0 g, 54.4 mmol). The mixture was stirred overnight, and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate, washed (brine (2×)), dried over Na2SO4 and filtered. The solvent was removed under reduced pressure, and the residue was purified on a silica gel column (eluting with PE/EA=10/1) to afford 1-(2-((tert-butyldimethylsilyl)oxy)ethyl)azocane (11.8 g, 88%). LCMS: 272 (M+H)+.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed (brine (2×))
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified on a silica gel column (eluting with PE/EA=10/1)

Sources & evidence

ORD record
ord-29910799cebf43319fe47c13dd450922
Source dataset
uspto-grants-2014_04
Patent number
US08703810B2

Reaction notes

Loading…