Acetic Acid → Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

HRID 1690674Notes

Reaction equation

HRID 1690674 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([OH:14])=[O:13])[CH:5]=[CH:4][C:3]1=2.[CH3:15][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>ClCCl.CO.O1CCCC1>[CH3:15][O:13][C:12]([C:6]1[CH:5]=[CH:4][C:3]2[C:2](=[O:1])[CH2:11][CH2:10][CH2:9][C:8]=2[CH:7]=1)=[O:14]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 28184935-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 15309116Methyl 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A sample of commercially available 5-Oxo-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid (200 mg, 1.05 mmol) is dissolved in a mixture of dichloromethane and methanol (5:1, 10 mL). The solution is then treated with a solution of trimethylsilyl diazomethane in tetrahydrofuran (2M) until the yellow color persists. The reaction is then treated with a small amount of acetic acid to destroy excess reagent and the solvent is removed. The residue is purified on silica gel to afford the title material as a yellow solid. ESMS m/z 204.1 (M+H+).

Workup

  1. customto destroy excess reagent
  2. customthe solvent is removed
  3. customThe residue is purified on silica gel

Sources & evidence

ORD record
ord-a6faedf54da84c1ea9e174aa2a51de5a
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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