Ethyl 3-(tributylsilyloxy)picolinate → 2-(4-Fluorobenzoyl)-3-(tributylsilyloxy)pyridine

HRID 429203Notes

Reaction equation

HRID 429203 reaction equation
[CH2:1]([Si:5]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:19][CH2:20][CH3:21])[O:6][C:7]1[C:8]([C:13]([O:15]CC)=O)=[N:9][CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH3:4].[F:26][C:27]1[CH:32]=[CH:31][C:30]([Mg]Cl)=[CH:29][CH:28]=1>O1CCCC1>[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:13]([C:8]2[C:7]([O:6][Si:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:18][CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:15])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 22987980Ethyl 3-(tributylsilyloxy)picolinateHCID 178505844HCID 178505844, compound

Product 1

HCID 229879642-(4-Fluorobenzoyl)-3-(tributylsilyloxy)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 3-(tributylsilyloxy)picolinate (19 g, 35 mmol) in tetrahydrofuran (100 ml) was cooled to 0° C. and 4-fluorophenylmagnesium chloride (52 ml, 1.0 M in tetrahydrofuran) was added dropwise. After 30 min., the reaction mixture was quenched with water and the product was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo. Purification on a silica gel column using ethyl acetate-hexane (2:98) as the eluant gave 2-(4-fluorobenzoyl)-3-(tributylsilyloxy)pyridine (3.75 g).

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionthe product was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification on a silica gel column

Sources & evidence

ORD record
ord-d954b17dc7fb47e3bee2a80ca170b2e4
Source dataset
uspto-grants-2001_11
Patent number
US06316464B1

Reaction notes

Loading…