Imidazole → tert-Butyl-(1-isobutyl-prop-2-ynyloxy)-dimethyl-silane

HRID 250533Notes

Reaction equation

HRID 250533 reaction equation
[CH3:1][CH:2]([CH3:8])[CH2:3][CH:4]([OH:7])[C:5]#[CH:6].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[C:17]([Si:14]([O:7][CH:4]([CH2:3][CH:2]([CH3:8])[CH3:1])[C:5]#[CH:6])([CH3:16])[CH3:15])([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 1438565-Methyl-1-hexyn-3-ol

Product 1

HCID 49851222tert-Butyl-(1-isobutyl-prop-2-ynyloxy)-dimethyl-silaneYield 97.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-methyl-hex-1-yn-3-ol (5.0 g, 0.045 mol) in dry DMF (50 mL) were added imidazole (3.64 g, 0.054 mol) and tert-butyldimethylsilyl chloride (6.06 g, 0.054 mol). The resulting mixture was stirred at RT for 2.5 h and then treated with saturated NH4Cl (25 mL) and EtOAc (250 mL). The organic layer was washed with saturated NH4Cl (50 mL), water (4×100 mL), brine (2×100 mL), dried over sodium sulfate, and concentrated in vacuo to afford the crude product (9.84 g, 97.5%), as a yellow oil, which was used in the next step without further purification. Rf 0.9 (EtOAc/hexanes 1/9); 1H NMR (CDCl3) δ 0.10 (s, 3H), 0.13 (s, 3H), 0.90-0.88 (m, 15H), 1.53-1.46 (m, 1H), 1.65-1.58 (m, 1H), 1.87-1.77 (septet, J=6.6 Hz, 1H), 2.36-2.35 (t, J=1.84 Hz, 1H), 4.39-4.37 (m, 1H).

Workup

  1. washThe organic layer was washed with saturated NH4Cl (50 mL), water (4×100 mL), brine (2×100 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bc6de72b5aa4197a7ea6739f27f66d4
Source dataset
uspto-grants-2011_01
Patent number
US07863312B2

Reaction notes

Loading…