Acetic Anhydride → 4-[1-Acetoxy-6-(2-pyridyl)hexyl]-2-trimethylsilylfuran

HRID 654937Notes

Reaction equation

HRID 654937 reaction equation
C([Li])(C)(C)C.Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[CH3:18][Si:19]([CH3:28])([CH3:27])[C:20]1[O:24][CH:23]=[C:22]([CH:25]=[O:26])[CH:21]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>CCCCC.O1CCCC1>[C:29]([O:26][CH:25]([C:22]1[CH:21]=[C:20]([Si:19]([CH3:28])([CH3:27])[CH3:18])[O:24][CH:23]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)(=[O:31])[CH3:30]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 156632515-(Trimethylsilyl)furan-3-carbaldehydeHCID 198859142-(5-Bromopentyl)pyridineHCID 178418306HCID 178418306, compound

Product 1

HCID 157233774-[1-Acetoxy-6-(2-pyridyl)hexyl]-2-trimethylsilylfuran

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

tert-Butyl lithium (a 1.7M solution in pentane; 2.4 ml, 4.14 mmol) was added dropwise to a solution of 2-(5-bromopentyl)pyridine (472.3 mg, 2.07 mmol) in tetrahydrofuran (7 ml) at -78° under argon. After 1 hour, a solution of 5-trimethylsilyl-3-furaldehyde (348 mg, 2.07 mmol) in tetrahydrofuran (1 ml) was added, followed by acetic anhydride (0.59 ml, 6.21 mmol) after 2 hours. The mixture was allowed to warm to room temperature and quenched with water (after 22 hours). Extraction (ethyl ether) and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was flash chromatographed on silica using 40% ethyl acetate/hexane. Fractions with Rf of about 0.25 on evaporation gave the title silyfuran as a light brown oil.

Workup

  1. customquenched with water (after 22 hours)
  2. extractionExtraction (ethyl ether) and evaporation of the
  3. dry with materialdried (magnesium sulphate)
  4. customextracts gave an oil, which
  5. customchromatographed on silica using 40% ethyl acetate/hexane
  6. customFractions with Rf of about 0.25 on evaporation
  7. customgave the title silyfuran as a light brown oil

Sources & evidence

ORD record
ord-8ccddbc0901546138fe1e1a012ad93b8
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

Loading…