Triethylsilane → Benzofuran, 2,3-dihydro-3-(phenylmethyl)-

HRID 256405Notes

Reaction equation

HRID 256405 reaction equation
[CH2:1]([C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:1]([CH:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 2826812HCID 2826812, compound

Product 1

HCID 11356275Benzofuran, 2,3-dihydro-3-(phenylmethyl)-Yield 20.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 19.5 g (91.4 mmole) 3-benzylbenzofuran in 75 ml trifluoroacetic acid was added 31.8 g (273 mmole) triethylsilane and the mixture was heated at reflux for six hours. The mixture was concentrated in vacuo, the residue diluted with water and extracted with ethyl ether. The ether extracts were carbon treated, the filtrate dried (Na2SO4) and the solvent evaporated to provide a dark oil. The oil was purified by silica gel column chromatography eluting with hexane, then its mixtures with ethyl ether. The combined product fractions were evaporated to provide 3.9 g (20%) of the title compound as a yellow oil. 1H-NMR(CDCl3)ppm(delta): 3.2 (m, 2H), 4.0 (m, 2H), 4.6 (t, 1H), 6.7-7.5 (m, 9H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for six hours
  3. concentrationThe mixture was concentrated in vacuo
  4. additionthe residue diluted with water
  5. extractionextracted with ethyl ether
  6. additiontreated
  7. dry with materialthe filtrate dried (Na2SO4)
  8. customthe solvent evaporated
  9. customto provide a dark oil
  10. customThe oil was purified by silica gel column chromatography
  11. washeluting with hexane
  12. customThe combined product fractions were evaporated

Sources & evidence

ORD record
ord-08d069b09644492482e418bf6420e747
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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