Imidazole → Ethyl 3-(tributylsilyloxy)picolinate

HRID 429202Notes

Reaction equation

HRID 429202 reaction equation
[OH:1][C:2]1[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:13]([Si:17](Cl)([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].N1C=CN=C1.O>C(Cl)Cl>[CH2:22]([Si:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[O:1][C:2]1[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)[CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 70448TributylchlorosilaneHCID 15080989Ethyl 3-hydroxypicolinate

Product 1

HCID 22987980Ethyl 3-(tributylsilyloxy)picolinateYield 49.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 3-hydroxypicolinate (15 g, 900 mmol), tributylsilyl chloride (16.23 g, 110 mmol), imidazole (8.0 g, 120 mmol) in methylene chloride was stirred overnight under a nitrogen atmosphere. Water was added and the methylene chloride layer was separated and concentrated in vacuo. Purification on a silica gel column using ethyl acetate-hexane (1:4) as the eluant gave ethyl 3-(tributylsilyloxy)picolinate as a solid (20 g).

Workup

  1. customthe methylene chloride layer was separated
  2. concentrationconcentrated in vacuo
  3. customPurification on a silica gel column

Sources & evidence

ORD record
ord-9fa13fd9f5084314bf9621baed61acfd
Source dataset
uspto-grants-2001_11
Patent number
US06316464B1

Reaction notes

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