Imidazole → HCID 59408054, compound

HRID 1799446Notes

Reaction equation

HRID 1799446 reaction equation
[CH2:1]([OH:13])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][OH:12].N1C=CN=C1.[CH3:19][C:20]([Si:23](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:22])[CH3:21]>CN(C)C=O>[Si:23]([O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:13])([C:20]([CH3:22])([CH3:21])[CH3:19])([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 8200Tetraethylene GlycolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 59408054HCID 59408054, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of tetra(ethylene glycol) 9 (5.00 mL, 28.7 mmol) and imidazole (2.91 g, 42.6 mmol) was dissolved in 10 mL of N,N-dimethylformamide (DMF). TBDPSCl (7.80 mL, 29.4 mmol) was added to the solution dropwise over a 30 min-period using a syringe with an additional amount of DMF (total 20 mL) being added to avoid the reaction mixture becoming cloudy. The reaction was stirred at room temperature for 16 h. DMF was removed under reduced pressure and the crude product was chromatographed (SiO2, gradient, hexane/EtOAc 1:1 to 2:3) to give 6.05 g (14.0 mmol, 49%) of 10 as a light colorless oil. Rf 0.21 (hexane/EtOAc 1:1); 1H NMR (400 MHz, CDCl3) δ 7.68 (m, 4H, H-2 of phenyl), 7.44-7.35 (m, 6H, H-3 and H-4 of phenyl), 3.81 (t, 2H, J=5.5 Hz, CH2OSi), 3.71 (m, 2H, HOCH2CH2), 3.68-3.58 (m, 12H, HOCH2CH2(OCH2CH2)2OCH2CH2), 2.46 (br s, 1H, OH), 1.05 (s, 9H, C(CH3)3); MS (ESI) Calcd for C24H36O5SiNa (M+Na+): 455.2. Found: 455.2.

Workup

  1. additionbeing added
  2. customDMF was removed under reduced pressure
  3. customthe crude product was chromatographed (SiO2, gradient, hexane/EtOAc 1:1 to 2:3)

Sources & evidence

ORD record
ord-2193f972ccd34ed2a5c6ae0ebd099f41
Source dataset
uspto-grants-2013_01
Patent number
US08344125B2

Reaction notes

Loading…