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

HRID 1090910Notes

Reaction equation

HRID 1090910 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 2.5M 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. 1H NMR (CDCl3) 0.81 (q, 6H, J=8.1 Hz), 0.99 (t, 9H, J=7.4 Hz), 5.14 (d, 1H, J=12.1 Hz), 5.48 (d, 1H, J=17.6 Hz), 6.64 (dd, 1H, J=10.8 Hz, 17.5 Hz), 6.81 (s, 1H) and 7.64 (s, 1H). HRMS exact mass calculated for C12H20SiO(M+) 208.1283, found 208.1280.

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-6f970d8ccaf94239a37f90ae264cdb12
Source dataset
uspto-grants-1992_01
Patent number
US05082954

Reaction notes

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