Imidazole → HCID 86608538, compound

HRID 1454101Notes

Reaction equation

HRID 1454101 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:12][CH:11]=1.N1C=CN=C1>CN(C)C=O>[Si:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11107524Benzyl 2-(4-hydroxyphenyl)acetate

Product 1

HCID 86608538HCID 86608538, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

t-Butyldimethylsilyl chloride (3.07 g, 20.4 mmol) was added in one portion to a stirred solution of benzyl (4-hydroxyphenyl)acetate (4.70 g, 19.4 mmol) and imidazole (1.39 g, 20.4 mmol) in dimethylformamide (25 mL) at room temperature under nitrogen. After stirring for 4 h the volatiles were evaporated and the residue partitioned between water (100 mL) and ethyl acetate (100 mL). The layers were separated and the aqueous phase washed with ethyl acetate (2×100 mL). The organic extracts were combined, dried (magnesium sulfate) and the solvent evaporated. The residue was chromatographed on silica gel (10% diethyl ether: cyclohexane) to give the title compound as a colourless oil (4.32 g, 62%). LC/MS: 4.13 min; z/e 374, calcd (M+18) 374. 1H NMR (400 MHz: CDCl3): 7.15 (5H), 6.95 (2H), 6.60 (2H), 4.95 (2H) 3.40 (2H), 0.8 (9H), 0.00 (6H).

Workup

  1. customwere evaporated
  2. customthe residue partitioned between water (100 mL) and ethyl acetate (100 mL)
  3. customThe layers were separated
  4. washthe aqueous phase washed with ethyl acetate (2×100 mL)
  5. dry with materialdried (magnesium sulfate)
  6. customthe solvent evaporated
  7. customThe residue was chromatographed on silica gel (10% diethyl ether: cyclohexane)

Sources & evidence

ORD record
ord-3a11f78612ad4944807b5e062b58994e
Source dataset
uspto-grants-2009_01
Patent number
US07476759B2

Reaction notes

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