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

HRID 963721Notes

Reaction equation

HRID 963721 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([SiH](CC)CC)C.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

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12052TriethylsilaneHCID 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 triethylsilane (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
  2. dry with materialHCl solution, sat. NaHCO3, and brine, dried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-41a49a8cfdbf4633b22ac1225d9bdc64
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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