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

HRID 1492932Notes

Reaction equation

HRID 1492932 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[Mg].Br[C:12]1[O:16][CH:15]=[C:14]([CH:17]=[O:18])[CH:13]=1.C([Li])(C)(C)C.Cl[Si:25]([CH3:28])([CH3:27])[CH3:26]>O1CCCC1.CCCCC>[OH:18][CH:17]([C:14]1[CH:13]=[C:12]([Si:25]([CH3:28])([CH3:27])[CH3:26])[O:16][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

8

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 81401-BromooctaneHCID 5462224MagnesiumHCID 150370565-Bromofuran-3-carbaldehydeHCID 178418306HCID 178418306, compound

Product 1

HCID 157287174-(1-Hydroxynonyl)-2-trimethylsilylfuran

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1-bromooctane (1.33 g, 6.9 mmol) and magnesium turnings (174 mg, 7.3 mmol) in tetrahydrofuran (8 ml) was refluxed under argon for 60 minutes. After cooling to 0°, a solution of 5-bromo-3-furaldehyde (1.21 g, 6.9 mmol) in THF (1 ml) was added and conditions maintained for 60 min. The mixture was further cooled to -78° and tert-butyl lithium (a 1.7M solution in pentane, 4.26 ml, 7.3 mmol) was added dropwise, followed by chlorotrimethylsilane (2.63 ml, 20.7 mmol) after 1 hour. Stirring was continued overnight 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 subjected to flash chromatography on silica using 15% ethyl ether/petroleum ether. Fractions with Rf of about 0.2 on evaporation gave the captioned compound as a yellow oil.

Workup

  1. temperaturewas refluxed under argon for 60 minutes
  2. temperatureAfter cooling to 0°
  3. temperatureconditions maintained for 60 min
  4. temperatureThe mixture was further cooled to -78°
  5. customThe mixture was quenched with saturated aqueous ammonium chloride
  6. additiondiluted with water (15 ml)
  7. extractionextracted with ether
  8. customEvaporation of the
  9. dry with materialdried (magnesium sulfate)
  10. extractionextract
  11. customgave a brown oil, which
  12. customFractions with Rf of about 0.2 on evaporation

Sources & evidence

ORD record
ord-d39e74fd1d5543dfaf7e761924dec827
Source dataset
uspto-grants-1994_12
Patent number
US05376676

Reaction notes

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