2-Methyl-3-hydroxy-4-acetyl-5-vinylpyridine → 2-Methyl-3-hydroxy-4-(2-hydroxybut-2-yl)-5-vinylpyridine

HRID 614399Notes

Reaction equation

HRID 614399 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([C:9](=[O:11])[CH3:10])[C:5]([CH:12]=[CH2:13])=[CH:4][N:3]=1.[CH2:14]([Mg]Br)[CH3:15]>O1CCCC1>[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([C:9]([OH:11])([CH2:14][CH3:15])[CH3:10])[C:5]([CH:12]=[CH2:13])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 202640462-Methyl-3-hydroxy-4-acetyl-5-vinylpyridineHCID 178418443HCID 178418443, compound

Product 1

HCID 202639952-Methyl-3-hydroxy-4-(2-hydroxybut-2-yl)-5-vinylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.93 g. of the product from Step A in 200 ml. of tetrahydrofuran was treated dropwise with 110% excess of ethyl magnesium bromide in tetrahydrofuran. After aging 2 days at ambient temperature the reaction was quenched on ice-water (100 ml.) containing 10 g. of ammonium chloride. The aqueous layer was separated and extracted with ether. The combined organic layers were dried over magnesium sulfate and evaporated to dryness to give 2-methyl-3-hydroxy-4-(2-hydroxybut-2-yl)-5-vinylpyridine, which was used directly in the next step.

Workup

  1. customthe reaction was quenched on ice-water (100 ml.)
  2. additioncontaining 10 g
  3. customThe aqueous layer was separated
  4. extractionextracted with ether
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-1487e0953e0e4e0fb2765c0fb55bb2a7
Source dataset
uspto-grants-1979_03
Patent number
US04144342

Reaction notes

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