Imidazole → HCID 68803997, compound

HRID 2369825Notes

Reaction equation

HRID 2369825 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14].N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21].CN(C)[CH:30]=[O:31]>C(OCC)(=O)C>[C:23]([Si:20]([CH3:22])([CH3:21])[O:31][CH2:30][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 141214-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-oneHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 68803997HCID 68803997, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4-Hydroxy-3-methoxy-phenyl)but-3-ene-2-one (4.402 g, 22.93 mmol) in N,N-dimethylformamide (28.5 mL) were added imidazole (1.71 g, 25.22 mmol) and tert-butyldimethylsilyl chloride (3.8 g; 25.22 mmol). The reaction was allowed to stir for 4 h, then diluted with ethyl acetate (300 mL) and washed with water (50 mL), saturated aqueous sodium bicarbonate (40 mL), and saturated aqueous sodium chloride (50 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated at reduced pressure to give crude product. Column purification on silica (8:2 hexanes/ethyl acetate) afforded 4-{4-[(tert-butyl-dimethyl-silanyloxy)-methyl}-3-methoxy-phenyl}-but-3-ene-2-one (5.24 g, 73% yield) as a solid: 1H NMR (400 MHz, CDCl3): δ 7.32 (d, 2H), 6.92 (m, 2H), 6.78 (d, 1H), 6.53 (d, 2H), 3.78 (s, 3H), 2.28 (s, 3H), 0.92 (s, 9H), 0.16 (s, 6H).

Workup

  1. washwashed with water (50 mL), saturated aqueous sodium bicarbonate (40 mL), and saturated aqueous sodium chloride (50 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated at reduced pressure
  5. customto give crude product
  6. customColumn purification on silica (8:2 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-973575e7ead14b91bb3fb835625e145b
Source dataset
uspto-grants-2014_04
Patent number
US08710038B2

Reaction notes

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