Trimethylsilyldiazomethane → HCID 61307061, compound

HRID 2368359Notes

Reaction equation

HRID 2368359 reaction equation
Cl.[NH2:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][OH:15])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].[CH3:16][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[NH2:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][OH:15])=[CH:8][C:4]=1[C:5]([O:7][CH3:16])=[O:6]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 12719196HCID 12719196, compound

Product 1

HCID 61307061HCID 61307061, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-Amino-5-(2-hydroxyethoxy)benzoic acid hydrochloride (0.209 g, 895 μmol; CAS 78299-60-2) was suspended in dichloromethane (10 ml) at r.t under an argon atmosphere. The reaction mixture was diluted with MeOH (3 ml). Then trimethylsilyldiazomethane solution (1.45 ml, 2.9 mmol; 2M in hexane) was added dropwise. The reaction mixture was stirred at r.t for 1 hr. The solvents were evaporated. The crude product was purified by silica gel chromatography using a n-heptane/EtOAc gradient to give the title compound (154 mg, 82%) as light yellow, waxy solid.

Workup

  1. customThe solvents were evaporated
  2. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-56129ba7f4be4018af5f83af6784e59c
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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