Imidazole → 4-Aminobenzyloxy-tert-butyldimethylsilane

HRID 1599831Notes

Reaction equation

HRID 1599831 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1.C1(O)C=CC=CC=1>C(Cl)Cl>[Si:10]([O:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([NH2:1])=[CH:3][CH:4]=1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 996PhenolHCID 28928tert-Butyldimethylsilyl chlorideHCID 693314-Aminobenzyl alcohol

Product 1

HCID 110754704-Aminobenzyloxy-tert-butyldimethylsilaneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-aminobenzyl alcohol (30.0 g, 81.2 mmol), tert-butyldimethylsilyl chloride (12.24 g, 81.2 mmol), imidazole (11.05 g, 162.4 mmol) and anhydrous CH2Cl2 (200 mL) was stirred at room temperature overnight. TLC analysis showed the appearance of a new spot and the disappearance of starting phenol. The solvent was removed in vacuo and then the remaining oily product was loaded onto a silica gel column and purified by chromatography, eluting with 3:1 hexane-ethyl acetate to afford 15.41 g (80%) of the title compound as a pale orange oil: 1H NMR (DMSO-d6) δ6.95 (d, J=8.4, 2H), 6.53 (d, J=8.4, 2H), 4.96 (s, 2H), 4.50 (s, 2H), 0.88 (s, 9H), 0.04 (s, 6H); 13C NMR (DMSO-d6) δ147.65, 128.04, 127.58, 113.57, 64.69, 25.82, 17.97, -5.18; MS (EI, m/z) 237 (M+).

Workup

  1. customThe solvent was removed in vacuo
  2. custompurified by chromatography
  3. washeluting with 3:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-b8bfcbde7688421aa0b03613ca782b94
Source dataset
uspto-grants-1998_04
Patent number
US05741926

Reaction notes

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