Trimethylsilyldiazomethane → Methyl 6-hydroxy-1-naphthoate

HRID 472780Notes

Reaction equation

HRID 472780 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]([OH:21])=[O:20])=[CH:14][CH:13]=[CH:12]2>CCOCC.C1COCC1>[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15]([C:19]([O:21][CH3:1])=[O:20])=[CH:14][CH:13]=[CH:12]2

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 11367671Methyl 6-hydroxy-1-naphthoateYield 56%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (trimethylsilyl)diazomethane (4.0 mL of a 2.0 M solution in Et2O, 8.0 mmol) was added slowly to a solution of 6-hydroxy-1-naphthoic acid (commercially available from TCI, 1.50 g, 8.0 mmol) in THF (40 mL) at 0° C. After 1.5 h at 0° C., the reaction mixture was concentrated in vacuo and absorbed onto silica. The resulting residue was purified on 80 g silica gel (100% hexanes→100% EtOAc, gradient) to afford 910 mg (56%) of methyl 6-hydroxy-1-naphthoate.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customabsorbed onto silica
  3. customThe resulting residue was purified on 80 g silica gel (100% hexanes→100% EtOAc, gradient)

Sources & evidence

ORD record
ord-66e2748f66224258858c75daa03b9fbd
Source dataset
uspto-grants-2014_01
Patent number
US08633220B2

Reaction notes

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