Tetrahydrofuran → HCID 86609625, compound

HRID 900505Notes

Reaction equation

HRID 900505 reaction equation
C1C[O:4]CC1.[CH2:6]([Si:8](Cl)([CH2:11][CH3:12])[CH2:9][CH3:10])[CH3:7].C([Si](CC)(CC)O[CH:18]=[C:19]([O:28][Si:29]([CH2:34][CH3:35])([CH2:32][CH3:33])[CH2:30][CH3:31])[O:20][Si:21]([CH2:26][CH3:27])([CH2:24][CH3:25])[CH2:22][CH3:23])C>>[CH2:6]([Si:8]([CH2:11][CH3:12])([CH2:9][CH3:10])[O:4][C:19]([O:28][Si:29]([CH2:30][CH3:31])([CH2:32][CH3:33])[CH2:34][CH3:35])([O:20][Si:21]([CH2:22][CH3:23])([CH2:26][CH3:27])[CH2:24][CH3:25])[CH3:18])[CH3:7]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 13819ChlorotriethylsilaneHCID 60147335HCID 60147335, compound

Product 1

HCID 86609625HCID 86609625, compound

Procedure

The ester was added to a 0.5 M THF (200 mL, 0.1 mol) solution over 15 minutes and the mixture was stirred at this temperature for an additional 15 minutes to generate the lithium enolate. Triethylsilyl chloride (16.7 mL 0.1 mol) was added over 15 minutes to trap the enolate as the tris(triethylsiloxy)ethene product. The mixture was warmed to ambient temperature and the THF solvent was removed by vacuum rotary evaporation at 40° C. to precipitate out the lithium chloride. The mixture was taken up in 300 mL of hexanes and 5 mL of triethylamine and stirred for 5 minutes while the salt was allowed to settle. The supernatant was twice filtered through a pad of diatomaceous earth to give a clear solution. The solution was concentrated under rotary evaporation to give the lightly yellow colored oil product.

Workup

  1. customthe THF solvent was removed by vacuum rotary evaporation at 40° C.
  2. customto precipitate out the lithium chloride
  3. stirring5 mL of triethylamine and stirred for 5 minutes while the salt
  4. filtrationThe supernatant was twice filtered through a pad of diatomaceous earth
  5. customto give a clear solution
  6. concentrationThe solution was concentrated under rotary evaporation
  7. customto give the lightly yellow colored oil product

Sources & evidence

ORD record
ord-bfd2691f49dd416b96f03b84c769752a
Source dataset
uspto-grants-2008_04
Patent number
US07358378B2

Reaction notes

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