Imidazole → HCID 58703542, compound

HRID 1179469Notes

Reaction equation

HRID 1179469 reaction equation
[Br:1][C:2]1[C:3]([O:14][CH2:15][O:16][CH3:17])=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:7]=1.N1C=CN=C1.[C:23]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])([CH3:25])[CH3:24].O>CN(C=O)C>[Br:1][C:2]1[C:3]([O:14][CH2:15][O:16][CH3:17])=[C:4]([CH:5]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:7]=1)[CH2:12][O:13][Si:27]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 58703546HCID 58703546, compound

Product 1

HCID 58703542HCID 58703542, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepare a solution of (3-bromo-2,5-bis-methoxymethoxy-phenyl)-methanol (1.46 g, 4.76 mmol) and imidazole (0.357 g, 5.24 mmol) in DMF (50 mL). Add tertbutyldimethylsilyl chloride (TBSCl) (0.790 g, 5.24 mmol). Stir the reaction for 3 hours and pour into cold H2O (150 mL). Extract the H2O with EtOAc (3×50 mL), combine the extracts, and wash with H2O (2×50 mL) and brine (20 mL). Dry (MgSO4), filter and concentrate to afford the subtitled product (1.95 g, >95%) as an oil that may be used without purification. 1NMR (CDCl3) δ 0.11 (s, 6H), 0.95 (s, 9H),3.47 (s, 3H), 3.51 (s, 3H), 4.84 (s, 2H), 5.02 (s, 2H), 5.12 (s, 2H), 7.15 (d, J=2.9 Hz, 1H), 7.17 (d, J=3.0 Hz, 1H).

Workup

  1. customthe reaction for 3 hours
  2. extractionExtract the H2O with EtOAc (3×50 mL)
  3. washwash with H2O (2×50 mL) and brine (20 mL)
  4. dry with materialDry (MgSO4)
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-e6186026f7704d84918c7c0c9d599ce6
Source dataset
uspto-grants-2007_10
Patent number
US07279499B2

Reaction notes

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