Imidazole → HCID 57907551, compound

HRID 403436Notes

Reaction equation

HRID 403436 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[Cl:14][C:15]1[CH:16]=[C:17]([CH:21]([OH:24])[CH:22]=[CH2:23])[CH:18]=[CH:19][CH:20]=1>>[C:4]([Si:1]([O:24][CH:21]([C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([Cl:14])[CH:16]=1)[CH:22]=[CH2:23])([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 14185029HCID 14185029, compound2×

Product 1

HCID 57907551HCID 57907551, compoundYield 46%

Procedure

To a solution of 22.4 g (133 mmol) of 1-(3-chlorophenyl)prop-2-en-1-ol in 90 mL anhydrous DMF (from Step A) was added t-butyldimethylsilyl chloride (20.0 g, 133 mmol) and imidazole (18.1 g, 266 mmol) and the resulting solution was stirred overnight under nitrogen at room temperature. Wash with water and extract with ethyl acetate. Separate organics, dry over magnesium sulfate, filter, and concentrate under vacuum. The residue was purified by flash silica gel column eluting with a gradient eluent of 0-15% ethyl acetate in hexane to afford the title compound (16.6 g, 46%). m/z (ES) 282, 284 (M, M+2)+; 151, 153 (M-OTBS, M-OTBS+2)+.

Workup

  1. washWash with water
  2. extractionextract with ethyl acetate
  3. dry with materialSeparate organics, dry over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under vacuum
  6. customThe residue was purified by flash silica gel column
  7. washeluting with a gradient eluent of 0-15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3fab74bea3c44abc96b8881be1b158b7
Source dataset
uspto-grants-2014_06
Patent number
US08748433B2

Reaction notes

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