Guaiacol → HCID 22733856, compound

HRID 1046927Notes

Reaction equation

HRID 1046927 reaction equation
[C:1]1([O:8][CH3:9])[C:2](=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:3].[CH3:10][CH:11]([Si:13](Cl)([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH3:12].N1C=CN=C1>CCOC(C)=O>[CH:11]([Si:13]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[O:3][C:2]1[CH:4]=[CH:5][CH:6]=[CH:7][C:1]=1[O:8][CH3:9])([CH3:12])[CH3:10]

Participants

5

Reactant 3

HCID 460GuaiacolHCID 795ImidazoleHCID 139400Triisopropylsilyl chloride

Product 1

HCID 22733856HCID 22733856, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

Guaiacol (2-methoxy-phenol, 34.6 mmol) is mixed with TIPSCl (51.9 mmol) and imidazole (103.8 mmol) in a tube. The mixture is heated in the microwave oven at 180° C. for 3 minutes. The oily mixture is diluted with EtOAc (100 mL) and washed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL). After drying over anhydrous Na2SO4, the filtrate is concentrated. The resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane) to yield triisopropyl-(2-methoxy-phenoxy)-silane as a colorless oil. Yield: 69%. 1H NMR (400 MHz, CDCl3) δ 6.8-6.89 (m, 4H), 3.8 (s, 3H), 1.22-1.28 (m, 3H), 1.1 (s, 9H), 1.08 (s, 9H). LC/MS (ES+): (M+1), 281.2. Rf=0.8 (5% EtOAc/hexane). (Note: Alternatively, conventional heating might be adopted in which case NMP is the solvent of choice).

Workup

  1. washwashed with NaHSO4 (1 M) (2×50 mL) and brine (50 mL)
  2. dry with materialAfter drying over anhydrous Na2SO4
  3. concentrationthe filtrate is concentrated
  4. customThe resultant crude mixture is purified by silica flash chromatography (2% EtOAc/hexane)

Sources & evidence

ORD record
ord-267fdf53516b4617a75c4d633e0c0969
Source dataset
uspto-grants-2013_10
Patent number
US08569345B2

Reaction notes

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