Imidazole → HCID 12007215, compound

HRID 2215755Notes

Reaction equation

HRID 2215755 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][OH:12])([O-:3])=[O:2].N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl>[C:21]([Si:18]([CH3:20])([CH3:19])[O:12][CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 270542-Nitrophenethyl alcoholHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 12007215HCID 12007215, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(2-nitro-phenyl)ethanol (10 g, 59 mmol) in CH2Cl2 (100 mL), was treated with imidazole (11.72 g, 77.7 mmol) followed by tert-butyl-dimethylsilylchloride (5.62 g, 82.6 mmol). A white precipitate formed upon the addition and the reaction was stirred 2.5 hours. The mixture was filtered and diluted with CH2Cl2 (100 mL) and was washed with 0.1 N HCl, H2O, saturated aq NaHCO3, and brine. The organic layer was dried over MgSO4, filtered and concentrated to give a transparent oil which was placed under high vacuum overnight to give the title compound (16.8 g, 100%) as a transparent oil. 1H NMR (400 MHz, DMSO-d6) −0.11 (s, 6H), 0.77 (s, 9H), 3.03 (t, J=6 Hz, 2H), 3.79 (t, J=6 Hz), 7.42–7.54 (m, 2H), 7.62 (ddd, J=<1, 6, 7 Hz, 1H), 7.88 (dd, J=<1, 7 Hz, 1H). MS (electrospray, m/z) 282 (M++1).

Workup

  1. customA white precipitate formed upon the addition
  2. filtrationThe mixture was filtered
  3. additiondiluted with CH2Cl2 (100 mL)
  4. washwas washed with 0.1 N HCl, H2O, saturated aq NaHCO3, and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a transparent oil which
  9. customwas placed under high vacuum overnight

Sources & evidence

ORD record
ord-d614124c6fdc40a39cfe23f27ecf0e38
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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