Imidazole → tert-Butyl(dimethyl)[(1-pentylprop-2-ynyl)oxy]silane

HRID 250531Notes

Reaction equation

HRID 250531 reaction equation
[CH:1]#[C:2][CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C.CCOCC>[C:13]([Si:10]([CH3:12])([CH3:11])[O:9][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:2]#[CH:1])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 131661-Octyn-3-olHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11791325tert-Butyl(dimethyl)[(1-pentylprop-2-ynyl)oxy]silaneYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-octyn-3-ol (5.0 g, 0.039 mol) in DMF (50 mL) were added tert-butyldimethylsilyl chloride (7.16 g, 0.0475 mol) and imidazole (3.2 g, 0.0475 mol). The resulting solution was stirred at RT for 18 h then diluted with ether (200 mL) and washed with water (2×200 mL), saturated solution of NH4Cl (200 mL), and brine (200 mL). The organic solution was dried over sodium sulfate and concentrated in vacuo to afford the desired compound (9.0 g, 95%) as a colorless oil used in the next step without further purification. Rf 0.9 (EtOAc/hexanes 1/9); 1H NMR (CDCl3) δ 0.09 (s, 3H), 0.12 (s, 3H), 0.89 (s, 9H), 0.85-1.00 (t, 3H), 1.20-1.70 (m, 8H), 2.35 (s, 1H), 4.30-4.35 (m, 1H).

Workup

  1. washwashed with water (2×200 mL), saturated solution of NH4Cl (200 mL), and brine (200 mL)
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b180c42e98a940b08668a5b15cdf5683
Source dataset
uspto-grants-2011_01
Patent number
US07863312B2

Reaction notes

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