2-(Tert-butyldimethylsilanyloxy)-1-phenylethanone → tert-Butyl-dimethyl-(2-phenyl-allyloxy)-silane

HRID 77325Notes

Reaction equation

HRID 77325 reaction equation
[CH2:1]([Li])CCC.[C:6]([Si:10]([CH3:22])([CH3:21])[O:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)([CH3:9])([CH3:8])[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:6]([Si:10]([CH3:22])([CH3:21])[O:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH2:1])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 2

HCID 135233382-(Tert-butyldimethylsilanyloxy)-1-phenylethanoneHCID 178418339Butyllithium

Product 1

HCID 67155247tert-Butyl-dimethyl-(2-phenyl-allyloxy)-silane

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a well stirred solution of methyl-triphenyl-phosphonium bromide (3.08 g, 8.61 mmol) in tetrahydrofuran (10 mL) at 0° C. is added n-butyllithium (4.89 mL, 7.83 mmol of a 1.6 M solution). The reaction mixture is allowed to warm to room temperature, stirred for 1 h, then cooled to 0° C. 2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethanone (980 mg, 3.91 mmol) in tetrahydrofuran (30 mL) is then slowly added. The mixture is stirred at room temperature for 30 min then quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted several times with ethyl acetate. The organic layers are combined, washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified via silica gel chromatography (20% ethyl acetate in hexanes) to yield 1.3 g of the title compound as a clear oil containing ethyl acetate and was used directly in the next step.

Workup

  1. temperaturecooled to 0° C
  2. stirringThe mixture is stirred at room temperature for 30 min
  3. customthen quenched by the addition of a saturated aqueous solution of ammonium chloride
  4. extractionextracted several times with ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified via silica gel chromatography (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b2a7d5ee0ce54511bfb46783c5186f6e
Source dataset
uspto-grants-2014_09
Patent number
US08841291B2

Reaction notes

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