Chlorotrimethylsilane → 4-(1-Hydroxyundecyl)-2-trimethylsilylfuran

HRID 654907Notes

Reaction equation

HRID 654907 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Mg].Br[C:14]1[O:18][CH:17]=[C:16]([CH:19]=[O:20])[CH:15]=1.C([Li])(C)(C)C.Cl[Si:27]([CH3:30])([CH3:29])[CH3:28]>C1COCC1.CCCCC>[OH:20][CH:19]([C:16]1[CH:15]=[C:14]([Si:27]([CH3:30])([CH3:29])[CH3:28])[O:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

8

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 81731-BromodecaneHCID 5462224MagnesiumHCID 150370565-Bromofuran-3-carbaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 198858964-(1-Hydroxyundecyl)-2-trimethylsilylfuran

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1-bromodecane (2.83 g, 13 mmol) and magnesium turnings (322 mg, 13.5 mmol) in THF (10 ml) was refluxed under argon for 60 min. After cooling to 0°, a solution of 5-bromo-3-furaldehyde (2.24 g, 13 mmol) in tetrahydrofuran (3 ml) was added and conditions maintained for 20 min. The mixture was further cooled to -78° and tert-butyl lithium (a 1.7M solution in pentane; 9.04 ml, 15.4 mmol) was added dropwise, followed by chlorotrimethylsilane (4.88 ml, 38.4 mmol) after 20 min. Stirring was continued overnight (12h) while the cooling bath attained room temperature. The mixture was quenched with saturated aqueous ammonium chloride, diluted with water (15 ml) and extracted with ether. Evaporation of the dried (magnesium sulfate) extract gave a brown oil, which was flash chromatographed on silica using 15% ethyl ether/petroleum ether. Fractions with about Rf 0.22 on evaporation gave the title compound as a yellow oil.

Workup

  1. temperaturewas refluxed under argon for 60 min
  2. temperatureAfter cooling to 0°
  3. temperatureconditions maintained for 20 min
  4. temperatureThe mixture was further cooled to -78°
  5. addition9.04 ml, 15.4 mmol) was added dropwise
  6. customwhile the cooling bath attained room temperature
  7. customThe mixture was quenched with saturated aqueous ammonium chloride
  8. additiondiluted with water (15 ml)
  9. extractionextracted with ether
  10. customEvaporation of the
  11. dry with materialdried (magnesium sulfate)
  12. extractionextract
  13. customgave a brown oil, which
  14. customchromatographed on silica using 15% ethyl ether/petroleum ether
  15. customFractions with about Rf 0.22 on evaporation

Sources & evidence

ORD record
ord-288355313818440fb41a1709f5754eff
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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