Benzaldehyde → 1-Phenyl-2-(trimethylsilyl)ethanol

HRID 1172324Notes

Reaction equation

HRID 1172324 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH4+].[Cl-].[CH3:11][Si:12]([CH2:15][Mg]Cl)([CH3:14])[CH3:13]>CCOCC>[C:2]1([CH:1]([OH:8])[CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 25517Ammonium ChlorideHCID 178418680HCID 178418680, compound

Product 1

HCID 125500031-Phenyl-2-(trimethylsilyl)ethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To benzaldehyde (2.17 g, 20.4 mmol) in 20 mL of ether, 1 M (trimethylsilyl)methyl magnesium chloride solution in ether (28.6 mL) was added at 0° C. After two hours of stirring at 0° C., a saturated NH4Cl solution was added and the mixture was extracted with ether (3×). The combined organic extract was dried (Na2SO4), filtered, and concentrated to give the title product (4.12 g).

Workup

  1. extractionthe mixture was extracted with ether (3×)
  2. extractionThe combined organic extract
  3. dry with materialwas dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d055074ea6804ddf800c0c68be116aab
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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