Thallous nitrate → 3-methoxy-1,2,3,4-tetrahydro-5H-benzocyclohepten-6-one

HRID 274048Notes

Reaction equation

HRID 274048 reaction equation
[N+]([O-])([O-])=[O:2].[Tl+].[CH2:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[CH2:10][CH2:9][CH2:8]1>CO.C(Cl)(Cl)Cl>[CH3:18][O:17][CH:14]1[CH2:13][CH2:12][C:11]2=[CH:10][CH:9]=[CH:8][C:6](=[O:2])[CH2:7][CH:16]2[CH2:15]1

Participants

5

Reactant 2

HCID 24937Thallous nitrateHCID 109650271-Methylene-7-methoxy-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 676857843-methoxy-1,2,3,4-tetrahydro-5H-benzocyclohepten-6-oneYield 70.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

To a solution of thallium nitrate (2.4 g) in methanol (24 ml) was added 1-methylene-7-methoxy-1,2,3,4-tetrahydronaphthalene (1.0 g) in methanol (7 ml) in one portion. The mixture was stirred for 1 minute and diluted with chloroform (24 ml). The resulting precipitate was filtered off and the filtrate was washed with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution; 8:1, n-hexane-ethyl acetate) to give 3-methoxy-1,2,3,4-tetrahydro-5H-benzocyclohepten-6-one (0.78 g).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washthe filtrate was washed with saturated aqueous sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (elution; 8:1, n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-5c6816d4a0254c81bc22b5e2cf0e7d37
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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