Hydrochloric Acid → HCID 15338763, compound

HRID 1769947Notes

Reaction equation

HRID 1769947 reaction equation
C([Mg]C[SiH](C)C)C1C=CC=CC=1.[Cl-].[CH2:14]([Si:21]([CH2:24]Cl)([CH3:23])[CH3:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Mg].[CH2:27]=[O:28].Cl>C(OCC)C.CCCCCC.C(OCC)C>[CH2:14]([Si:21]([CH3:23])([CH3:22])[CH2:24][CH2:27][OH:28])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 4046821Benzyl(chloromethyl)dimethylsilaneHCID 5462224MagnesiumHCID 178504352HCID 178504352, compound

Product 1

HCID 15338763HCID 15338763, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21584099Diethylether hexaneSolvent

Procedure

To a solution of benzyldimethylsilylmethyl magnesium chloride, prepared from benzylchloromethyldimethyl silane (Fessenden, R. J., Coon, M. D., J. Med. Chem. Vol. 9 pp. 262-263 (1966)) (1.5 g, 7.55 mmol) and magnesium (0.19 g, 7.9 mmol) in diethyl ether (15 ml), is added paraformaldehyde (0.228 g, 7.6 mmol). Then the mixture is refluxed for 18 hours, cooled to 0° C. and hydrolyzed with 1N HCl (25 ml). The organic layer is washed with water brine and dried over MgSO4. The solution is filtered and solvent removed invacuo. Chromatography (silica gel, hexane/diethyl ether 70/30) afforded β-(benzyldimethylsilyl)ethanol as an oil (0.84 g, 57% yield). m.p. 132°-133° C.

Workup

  1. temperatureThen the mixture is refluxed for 18 hours
  2. washThe organic layer is washed with water brine
  3. dry with materialdried over MgSO4
  4. filtrationThe solution is filtered
  5. customsolvent removed invacuo

Sources & evidence

ORD record
ord-1f9f0e69720e49608291a8d2c46aa23b
Source dataset
uspto-grants-1995_01
Patent number
US05384312

Reaction notes

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