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

HRID 986974Notes

Reaction equation

HRID 986974 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-dfd6cafa8a334d39b6085f772452719f
Source dataset
uspto-grants-2003_10
Patent number
US06630485B2

Reaction notes

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