Tetrahydrofuran → 2-Methylenetetralin-1-one

HRID 1252796Notes

Reaction equation

HRID 1252796 reaction equation
[C:1]1(=[O:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:12]1COCC1>>[CH2:12]=[C:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]1=[O:11]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 107241-Tetralone

Product 1

HCID 3777512-Methylenetetralin-1-one

Procedure

To a solution of 1-tetralone (164.5 g) in about 400 ml THF was added, in four separate portions, TAMA (243 g) and trioxymethylene (99 g) over 31/2 hours, and the mixture refluxed for 20 hours. The mixture was cooled and portioned between Et2O and water, the layers separated and the aqueous layer extracted twice with Et2O. The combined Et2O layers are exhaustively washed with water, NaHCO3 and then with brine, dried (MgSO4) concentrated in vacuo to yield an oil which is flash chromatographed on silica gel using CH2Cl2 in several runs of 10-20 g per run. Fractions containing the fast moving material are combined, concentrated in vacuo to obtain the desired 2-methylene-1-tetralone.

Workup

  1. customseparate portions, TAMA (243 g) and trioxymethylene (99 g) over 31/2 hours
  2. temperaturethe mixture refluxed for 20 hours
  3. temperatureThe mixture was cooled
  4. customthe layers separated
  5. extractionthe aqueous layer extracted twice with Et2O
  6. washThe combined Et2O layers are exhaustively washed with water, NaHCO3
  7. dry with materialwith brine, dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto yield an oil which
  10. customchromatographed on silica gel
  11. additionFractions containing the
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87df41a277fd45a8b0929fa1e84f849b
Source dataset
uspto-grants-1988_05
Patent number
US04745222

Reaction notes

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