Chlorotrimethylsilane → (4-Ethylphenyl)(2-methoxyphenyl)methane

HRID 1182029Notes

Reaction equation

HRID 1182029 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])O)=[CH:5][CH:4]=1)[CH3:2].C([BH3-])#N.[Na+].C[Si](Cl)(C)C>C(#N)C>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 17964395HCID 17964395, compound

Product 1

HCID 17964392(4-Ethylphenyl)(2-methoxyphenyl)methaneYield 66.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

1.34 g of (4-ethylphenyl)(2-methoxyphenyl)methanol are dissolved in acetonitrile and cooled to 0° C. 1.50 g of sodium cyanoborohydride are added to the mixture and then 3.00 ml of trimethylsilyl chloride are added. The mixture is stirred at room temperature overnight. The reaction solution is filtered through Celite and extracted with saturated NaCl solution. The organic phase is dried over sodium sulfate and concentrated. The crude product is chromatographed on silica gel with ethyl acetate/heptane (1/12). 0.83 g of the product is obtained. C16H180 (226.32) MS (DCl) 227.4 (M+H+)

Workup

  1. filtrationThe reaction solution is filtered through Celite
  2. extractionextracted with saturated NaCl solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product is chromatographed on silica gel with ethyl acetate/heptane (1/12)

Sources & evidence

ORD record
ord-5c3be5bc0eac49ffa62bde7ab2bc25f8
Source dataset
uspto-grants-2007_10
Patent number
US07288528B2

Reaction notes

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