Imidazole → Tert-butyl-dimethyl-(2-methyl-2-p-tolyl-propoxy)-silane

HRID 23792Notes

Reaction equation

HRID 23792 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4].N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].O>CN(C=O)C>[C:21]([Si:18]([CH3:20])([CH3:19])[O:4][CH2:3][C:2]([CH3:1])([C:6]1[CH:7]=[CH:8][C:9]([CH3:12])=[CH:10][CH:11]=1)[CH3:5])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 132166942,2-Dimethyl-2-(4-methylphenyl)ethanol

Product 1

HCID 22590506Tert-butyl-dimethyl-(2-methyl-2-p-tolyl-propoxy)-silaneYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methyl-2-p-tolyl-propan-1-ol (405 mg, 2.46 mmol) in DMF (5 mL) was added imidazole (335 mg, 4.92 mmol) followed by tert-butyldimethylsilyl chloride (465 mg, 3.08 mmol). The reaction was stirred for 24 h and water was added. The aqueous solution was washed with EtOAc (3×). The combined organic solutions were washed with water (4×). The organic solution was dried (MgSO4), filtered and concentrated. Medium pressure chromatography (hexanes) provided tert-butyl-dimethyl-(2-methyl-2-p-tolyl-propoxy)-silane (619 mg). 1H NMR (400 MHz, CDCl3) δ 7.26 (d, 2H), 7.10 (d, 2H), 3.49 (s, 2H), 2.31 (s, 3H), 1.27 (s, 6H), 0.85 (s, 9H), −0.06 (s, 6H).

Workup

  1. washThe aqueous solution was washed with EtOAc (3×)
  2. washThe combined organic solutions were washed with water (4×)
  3. dry with materialThe organic solution was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ecf2c2ce7e084beaaf076587f4f87ba6
Source dataset
uspto-grants-2005_02
Patent number
US06852863B2

Reaction notes

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