2-({[Tert-butyl(dimethyl)silyl]oxy}methyl)butanal → Tert-butyl[(2-ethylbut-3-en-1-yl)oxy]dimethylsilane

HRID 551707

Reaction equation

HRID 551707 reaction equation
[CH2:1]([Li])CCC.[Si:6]([O:13][CH2:14][CH:15]([CH2:18][CH3:19])[CH:16]=O)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[C:9]([Si:6]([O:13][CH2:14][CH:15]([CH2:18][CH3:19])[CH:16]=[CH2:1])([CH3:8])[CH3:7])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 108464032-({[Tert-butyl(dimethyl)silyl]oxy}methyl)butanalHCID 178418339Butyllithium

Product 1

HCID 86646162Tert-butyl[(2-ethylbut-3-en-1-yl)oxy]dimethylsilane

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

(Methyl)triphenylphosphonium bromide (59.1 g, 165 mmol) was suspended in tetrahydrofuran (330 mL). To the suspension, n-butyllithium (1.57 M hexane solution, 97.3 mL, 153 mmol) was gradually added with stirring at 0° C. The mixture was stirred at this temperature for 1 hour, and a tetrahydrofuran solution (110 mL) of 2-({[tert-butyl(dimethyl)silyl]oxy}methyl)butanal (Tetrahedron 2004, 60, 9307) (27.6 g, 127 mmol) was then gradually added thereto. The mixture was stirred at 0° C. for 2 hours, and the reaction was then terminated by the addition of a saturated aqueous solution of ammonium chloride and water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of ammonium chloride, water, and saturated saline and then dried over anhydrous sodium sulfate. The residue was filtered and concentrated under reduced pressure. Then, the obtained crude product was purified by silica gel column chromatography to obtain the compound of interest as an oil substance (19.9 g, 73%).

Workup

  1. stirringThe mixture was stirred at this temperature for 1 hour
  2. stirringThe mixture was stirred at 0° C. for 2 hours
  3. customthe reaction was then terminated by the addition of a saturated aqueous solution of ammonium chloride and water
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of ammonium chloride, water, and saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe residue was filtered
  8. concentrationconcentrated under reduced pressure
  9. customThen, the obtained crude product
  10. customwas purified by silica gel column chromatography
  11. customto obtain the compound of interest as an oil substance (19.9 g, 73%)

Sources & evidence

ORD record
ord-36b39e91f59f450ab6c28f6a0d0bc785
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Linked notes

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