3-Furancarboxaldehyde, 5-(triethylsilyl)- → HCID 11830655, compound

HRID 1109890Notes

Reaction equation

HRID 1109890 reaction equation
[CH2:1]([Li])CCC.[CH2:6]([Si:8]([CH2:18][CH3:19])([CH2:16][CH3:17])[C:9]1[O:10][CH:11]=[C:12]([CH:14]=O)[CH:13]=1)[CH3:7]>CCCCCC.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:6]([Si:8]([CH2:18][CH3:19])([CH2:16][CH3:17])[C:9]1[O:10][CH:11]=[C:12]([CH:14]=[CH2:1])[CH:13]=1)[CH3:7]

Participants

6

Reactant 2

HCID 108784383-Furancarboxaldehyde, 5-(triethylsilyl)-HCID 178418339Butyllithium

Product 1

HCID 11830655HCID 11830655, compound

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

n-Butyl lithium (a 2.5 M solution in hexane; 4.4 ml, 11.0 mmol) was added dropwise to a suspension of methyltriphenylphosphonium bromide (3.93 g, 11 mmol) in THF (40 ml) at 0 degrees C. under argon. After 2 hours stirring at 0 degrees C., a solution of 2-triethylsilyl-4-furaldehyde (1.54 g, 7.33 mmol) in THF (2 ml) was added. Stirring was continued at room temperature for 14 hours and the mixture was quenched with methanol/water 40 ml (1:1). Extraction (pentane) and evaporation of the dried (magnesium sulfate) extracts gave a residue, which was purified by flash chromatography on silica using pentane to give the titled furan. Rf (pentane) 0.75.

Workup

  1. stirringStirring
  2. waitwas continued at room temperature for 14 hours
  3. customthe mixture was quenched with methanol/water 40 ml (1:1)
  4. extractionExtraction (pentane) and evaporation of the
  5. dry with materialdried (magnesium sulfate)
  6. customextracts gave a residue, which
  7. customwas purified by flash chromatography on silica

Sources & evidence

ORD record
ord-81ebcf25bfd9442f9cad51e0e493d46a
Source dataset
uspto-grants-1994_06
Patent number
US05322953

Reaction notes

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