Imidazole → HCID 58250168, compound

HRID 1045077Notes

Reaction equation

HRID 1045077 reaction equation
[Br:1][CH:2](O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[Si:15](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CN=C1.[OH2:38]>CN(C=O)C.C(OCC)C>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:38][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 21122189HCID 21122189, compound

Product 1

HCID 58250168HCID 58250168, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

1-Bromododecanol (2.511 g, 9.47 mmol), tert-butyldiphenylsilylchloride (2.66 mL, 15.15 mmol), and imidazole (1.418 g, 20.83 mmol) were dissolved in dry DMF (20 mL) and the resulting mixture was stirred under nitrogen for 3 h at room temperature. Upon completion of reaction, water (15 mL) and diethyl ether (25 mL) were added, the two layers were separated and the water layer was extracted with diethyl ether (3×25 mL). The combined organic extracts were washed with water, brine, dried over MgSO4, filtered and filtrate evaporated. The crude was purified by silica gel column chromatography using 100% hexane to 5% ethyl acetate/hexane as eluent to afford the title product as a clear thick oil (3.57 g, 75%). 1H NMR (CDCl3): δ7.66 (m, 4H), 7.39 (m, 6H), 3.62 (t, 2H, J=6.5 Hz), 3.40 (t, 2H, J=6.9 Hz), 1.85 (m, 2H), 1.54 (m, 2H), 1.44-1.25 (m, 16H), 1.04 (s, 9H). m/z (APCI) 505.37 (M++1).

Workup

  1. additionwere added
  2. customthe two layers were separated
  3. extractionthe water layer was extracted with diethyl ether (3×25 mL)
  4. washThe combined organic extracts were washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customfiltrate evaporated
  8. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0b895bfbf98641f686ff5dc7e4e460a6
Source dataset
uspto-grants-2013_10
Patent number
US08563760B2

Reaction notes

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