Ethanol → HCID 20263956, compound

HRID 464091Notes

Reaction equation

HRID 464091 reaction equation
C(O[S:5][CH2:6][CH3:7])(=O)C.[O-:8][CH2:9][CH3:10].[Na+].Br.BrC1[C:19]([CH:20]=[CH2:21])=[CH:18][N:17]=[C:16]([CH3:22])[C:15]=1[OH:23].[CH2:24]([OH:26])[CH3:25]>>[CH2:9]([O:8][C:24]([CH2:25][S:5][CH2:6][C:7]1[C:19]([CH:20]=[CH2:21])=[CH:18][N:17]=[C:16]([CH3:22])[C:15]=1[OH:23])=[O:26])[CH3:10]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 2723922Sodium ethoxideHCID 20263993HCID 20263993, compoundHCID 20381866HCID 20381866, compound

Product 1

HCID 20263956HCID 20263956, compound

Procedure

To an ice cold mixture of 0.01 mole of ethylmercapto acetate and 0.02 mole of sodium ethoxide in 100 ml. ethanol under nitrogen is added a solution of 4-bromo-3-hydroxy-2-methyl-5-vinylpyridine hydrobromide in 50 ml. of ethanol. The reaction mixture is stirred overnight at room temperature, concentrated in vacuo and taken up between ethyl acetate and water. The organic layer is separated, washed well with water, dried and concentrated. Chromatography of the residue on silica gel-elution with ether-petroleum ether 10-50% gives 4-ethoxycarbonylmethylthiomethyl-3-hydroxy-2-methyl-5-vinyl pyridine.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe organic layer is separated
  3. washwashed well with water
  4. customdried
  5. concentrationconcentrated
  6. washChromatography of the residue on silica gel-elution with ether-petroleum ether 10-50%

Sources & evidence

ORD record
ord-755b437551cf4d6383503c2bbe4e042e
Source dataset
uspto-grants-1985_10
Patent number
US04546106

Reaction notes

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