Imidazole → HCID 12007215, compound

HRID 751479Notes

Reaction equation

HRID 751479 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6][CH2:7][OH:8])([O-:3])=[O:2].N1C=CN=C1.ClCCl.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(OCC)(=O)C.C(OCC)C>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[CH2:6][CH2:7][O:8][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 270542-Nitrophenethyl alcoholHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 12007215HCID 12007215, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Add 2-nitrophenethyl alcohol (20 g, 120 mmol) and imidazole (11.4 g, 167 mmol) to dichloromethane (200 mL). Cooled to 0° C. and add solid tert-butyldimethylsilyl chloride (23.4 g, 155 mmol). Stir the mixture at 20° C. for 2 hours and dilute with 1:1 ethyl acetate:diethyl ether. Wash with distilled water, aqueous 3% acetic acid, aqueous 0.5 molar sodium hydrogen carbonate, and saturated sodium chloride. Dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure to give 32.4 g (96%) of the title compound as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.89 (dd, 1H, J=8.0, 1.2 Hz), 7.50 (dt, 1H, J=7.2, 1.6 Hz), 7.37 (m, 2H), 3.89 (t, 2H, J=6.4 Hz), 3.12 (t, 2H, J=6.4 Hz), 0.83 (s, 9H), 0.06 (s, 6H).

Workup

  1. washWash with distilled water, aqueous 3% acetic acid, aqueous 0.5 molar sodium hydrogen carbonate, and saturated sodium chloride
  2. dry with materialDry over anhydrous magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-3596fd6ee1b04584884deaf9d3711d58
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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