Hexane → HCID 10414091, compound

HRID 1109069Notes

Reaction equation

HRID 1109069 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][N:10]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.CCCCCC.[Br:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]Br>O1CCCC1.O>[Br:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:9]1[N:10]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 123681,6-DibromohexaneHCID 102473344,5-diphenyl-1-[(trimethylsilyl)ethoxymethyl]-1H-imidazoleHCID 178418339Butyllithium

Product 1

HCID 10414091HCID 10414091, compoundYield 385.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Part A. To a solution of 4,5-diphenyl-1-[(trimethylsilyl)ethoxymethyl]-1H-imidazole (2.5 g, 0. 00734 mol) (B. Lipshutz, B. Huff, W. Hazen, Tetrahedron Letters, 29, 3411-14, 1988), in dry tetrahydrofuran (50 mL) cooled to -78° under a nitrogen atmosphere, n-butyl lithium in hexane (2.5M, 0.00734 mol) was added slowly. The reaction mixture was stirred for 1 hour and 1,6-dibromohexane (2.68 g, 0.0011 mol) was added rapidly, stirred for 1/2 hour and was allowed to warm to ambient temperature and stirred for 2 additional hours. The reaction mixture was poured into water and extracted with ethyl acetate (2×50 mL). The combined organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give a viscous oil. The product was purified by flash chromatography on silica gel (250 mL) eluting with hexane:ethyl acetate (70:30 v:v) to give 6-bromo-1-(4,5-diphenyl-1-[(trimethylsilyl)ethoxymethyl]imidazol-2-yl)hexane as an oil (2.18 g, 0.00424 mol). 1H NMR (CDCl3) δ 7.53-7.16(m,10H), 5.10(s,2H), 3.48(t,2H), 3.34(t,2H), 2.90(t,2H), 1.99-1.5 (m,8H), 0.875(t,2H), 0.008(s,9H).

Workup

  1. stirringstirred for 1/2 hour
  2. stirringstirred for 2 additional hours
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customto give a viscous oil
  8. customThe product was purified by flash chromatography on silica gel (250 mL)
  9. washeluting with hexane:ethyl acetate (70:30 v:v)

Sources & evidence

ORD record
ord-6a6e8034733a4cd98af33d754f6a42f0
Source dataset
uspto-grants-1994_06
Patent number
US05318984

Reaction notes

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