Imidazole → (E)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-styryloxazole

HRID 82816Notes

Reaction equation

HRID 82816 reaction equation
N#N.[CH:3](/[C:11]1[O:12][CH:13]=[C:14]([CH2:16][OH:17])[N:15]=1)=[CH:4]\[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].N1C=CN=C1>C(Cl)Cl.O>[Si:22]([O:17][CH2:16][C:14]1[N:15]=[C:11](/[CH:3]=[CH:4]/[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:12][CH:13]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 947NitrogenHCID 28928tert-Butyldimethylsilyl chlorideHCID 13657827(E)-(2-Styryloxazol-4-yl)methanol

Product 1

HCID 67958594(E)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-styryloxazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (E)-(2-styryloxazol-4-yl)methanol (5.40 g, 26.8 mmol) in CH2Cl2 (56.0 mL) was treated at rt with tert-butylchlorodimethylsilane (8.52 g, 53.67 mmol) followed by imidazole (3.69 g, 53.67 mmol) and the resulting suspension was stirred for 1 h at rt. Water was added. The aq. layer was extracted with and the combined org. layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (gradient from hept to 9:1 hept-EA) gave the title compound as a yellow oil. TLC: rf (9:1 hept-EA)=0.35. LC-MS-conditions 07: tR=1.08 min, [M+H]+=316.13.

Workup

  1. extractionThe aq. layer was extracted with and the combined org
  2. dry with materiallayers were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customPurification of the residue by FC (gradient from hept to 9:1 hept-EA)

Sources & evidence

ORD record
ord-a71a52c9f76a43e2910c52b2481e0fc6
Source dataset
uspto-grants-2014_09
Patent number
US08846733B2

Reaction notes

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