Imidazole → 5-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid methyl ester

HRID 2065001Notes

Reaction equation

HRID 2065001 reaction equation
N#N.[CH3:3][O:4][C:5]([C:7]1[N:8]=[CH:9][O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][OH:20])[CH:13]=1)=[O:6].[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N1C=CN=C1.[NH4+].[Cl-]>C1COCC1.CC(=O)OCC>[CH3:3][O:4][C:5]([C:7]1[N:8]=[CH:9][O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:13]=1)=[O:6]

Participants

8

Reactant 5

HCID 795ImidazoleHCID 947NitrogenHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 669288215-[3-(2-Hydroxy-ethyl)-phenyl]-oxazole-4-carboxylic acid methyl ester

Product 1

HCID 669282965-{3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-oxazole-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), 5-[3-(2-hydroxy-ethyl)-phenyl]-oxazole-4-carboxylic acid methyl ester (200 mg, 0.81 mmol) was dissolved in dry THF (5.0 mL). tert-Butyldimethylsilyl chloride (124 mg, 0.83 mmol) was added at 0° C. followed by imidazole (61 mg, 0.89 mmol). The reaction mixture was stirred at rt for 2 days. Sat. aq. NH4Cl (10 mL) and EA (10 mL) were added, the layers separated and the aq. layer extracted with EA (2×10 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (20:80 hept-EA) gave the title compound as a colorless oil. TLC: rf (20:80 hept-EA)=0.21. LC-MS-conditions 02: tR=1.19 min, [M+H]+=362.50.

Workup

  1. customthe layers separated
  2. extractionthe aq. layer extracted with EA (2×10 mL)
  3. dry with materialextracts were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customPurification of the residue by FC (20:80 hept-EA)

Sources & evidence

ORD record
ord-5d4e6e6dbb454bc1a747b75fb60b5a83
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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