1-Bromododecane → 3-(1-Hydroxytridecyl)-5-trimethylsilylfuran

HRID 1534336Notes

Reaction equation

HRID 1534336 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[Mg].[CH3:15][Si:16]([CH3:25])([CH3:24])[C:17]1[O:21][CH:20]=[C:19]([CH:22]=[O:23])[CH:18]=1>O1CCCC1>[OH:23][CH:22]([C:19]1[CH:18]=[C:17]([Si:16]([CH3:25])([CH3:24])[CH3:15])[O:21][CH:20]=1)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH3:2]

Participants

5

Reactant 3

HCID 89191-BromododecaneHCID 5462224MagnesiumHCID 156632515-(Trimethylsilyl)furan-3-carbaldehyde

Product 1

HCID 156632683-(1-Hydroxytridecyl)-5-trimethylsilylfuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 1-bromododecane (2.97 g, 11.9 mmol) and magnesium turnings (300 mg, 12.5 mmol) in tetrahydrofuran (20 ml) was refluxed under argon for 30 minutes. On cooling, a solution of 5-trimethylsilyl-3-furaldehyde (1g, 5.9 mmol) in tetrahydrofuran (THF) (2 ml) was added. After 30 min., the reaction mixture was quenched with saturated ammonium chloride. Extraction (ethyl ether), drying (magnesium sulfate) and evaporation afforded an oil, which was purified by flash chromatography on silica using 15% ethyl ether/hexane. Fractions with Rf of about 0.25 on evaporation gave the title alcohol as a pale yellow oil, which solified into a colorless solid on storage at -20°.

Workup

  1. temperaturewas refluxed under argon for 30 minutes
  2. temperatureOn cooling
  3. customthe reaction mixture was quenched with saturated ammonium chloride
  4. extractionExtraction (ethyl ether)
  5. customdrying
  6. custom(magnesium sulfate) and evaporation
  7. customafforded an oil, which
  8. customwas purified by flash chromatography on silica using 15% ethyl ether/hexane
  9. customFractions with Rf of about 0.25 on evaporation

Sources & evidence

ORD record
ord-57f3f53d9dc94918a7097a536e2d6fcd
Source dataset
uspto-grants-1992_02
Patent number
US05089485

Reaction notes

Loading…