Water → 2-Methyl-2-methoxycarbonyl-5-methoxy-1,2,3,4-tetrahydronaphthalene

HRID 344050Notes

Reaction equation

HRID 344050 reaction equation
[CH3:1][C:2]1([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH3:13])[C:3]1=O.C(OCC)(=O)C.O>FC(F)(F)C(O)=O>[CH3:1][C:2]1([C:15]([O:17][CH3:18])=[O:16])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[O:12][CH3:13])[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 543642852-Methyl-2-methoxycarbonyl-5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 540790102-Methyl-2-methoxycarbonyl-5-methoxy-1,2,3,4-tetrahydronaphthaleneYield 211.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2-methyl-2-methoxycarbonyl-5-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene (2.0 g) in trifluoroacetic acid (20 ml) was added triethyls4lane (2.0 ml) at room temperature. After being stirred for 6 hours at room temperature, the solution was poured into a mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 2-methyl-2-methoxycarbonyl-5-methoxy-1,2,3,4-tetrahydronaphthalene (4.0 g).

Workup

  1. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7de90438cf35409cb694fb99addffe1e
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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