2-Methyl-3-hydroxy-4-acetyl-5-vinylpyridine → HCID 20263995, compound

HRID 223521Notes

Reaction equation

HRID 223521 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 20263995HCID 20263995, compound

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-441a3bfd67f3454286c7976e9d4cf5c0
Source dataset
uspto-grants-1982_10
Patent number
US04355034

Reaction notes

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