Trimethylsilyldiazomethane → Methyl 6-methoxy-2-naphthoate

HRID 23226Notes

Reaction equation

HRID 23226 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([OH:15])=[O:14])[CH:7]=[CH:6]2.[Si](C=[N+]=[N-])(C)(C)[CH3:17]>C1C=CC=CC=1.CO>[CH3:17][O:14][C:13]([C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1)=[O:15]

Participants

4

Reactant 2

HCID 167693Trimethylsilyldiazomethane2×HCID 3491816-Methoxy-2-Naphthoic Acid

Product 1

HCID 604020Methyl 6-methoxy-2-naphthoateYield 81%

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

To a stirred solution of 6-methoxy-2-naphthoic acid (10.0 g, 49.5 mmol) in benzene:MeOH (4:1, 200 mL) at 0° C. was added TMS diazomethane (29.7 mL, 2.0 M in hexnae, 59.4 mmol) dropwise. After initial addition of reagent, TLC showed reaction was not quite complete, so another 4 mL of TMS diazomethane added. The reaction was then stirred for 1 h before total completion. After concentration, the residue was recrystallized from MeOH:H2O to afford the product (8.67 g, 81%) as a solid; 1H NMR (DMSO-d6) δ3.85 (s, 3H), 3.87 (s, 3H), 7.22 (dd, J=2.6, 9.0 Hz, 1H), 7.37 (d, J=2.4 Hz, 1H), 7.85-7.92 (m, 2H), 8.00 (d, J=9.0 Hz, 1H), 8.51 (s, 1H); mass spectrum [(+) ESI], m/z 217 (M+H)+.

Workup

  1. additionAfter initial addition of reagent, TLC
  2. customreaction
  3. concentrationAfter concentration
  4. customthe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-3c29bb0a3e474e1aabf5198a3ac40b45
Source dataset
uspto-grants-2005_02
Patent number
US06849761B2

Reaction notes

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