Hydrochloric Acid → HCID 15338763, compound

HRID 260634Notes

Reaction equation

HRID 260634 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 in vacuo. Chromatography (silica gel, hexane/diethyl ether 70/30) afforded β-(benzyldimethylsilyl)ethanol as an oil (0.84 g, 57% yield).

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 in vacuo

Sources & evidence

ORD record
ord-8ab803b5e8bd4334aa80466ff52f51bd
Source dataset
uspto-grants-1996_06
Patent number
US05529988

Reaction notes

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