Acetic Anhydride → 2-Methyl-3-acetoxy-4-acetylthiomethyl-5-vinylpyridine

HRID 1856015Notes

Reaction equation

HRID 1856015 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][C:9]1[C:14]([OH:15])=[C:13]([CH2:16][SH:17])[C:12]([CH:18]=[CH2:19])=[CH:11][N:10]=1.[O:20]1CC[CH2:22][CH2:21]1>>[CH3:8][C:9]1[C:14]([O:15][C:1](=[O:3])[CH3:2])=[C:13]([CH2:16][S:17][C:21](=[O:20])[CH3:22])[C:12]([CH:18]=[CH2:19])=[CH:11][N:10]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8028Tetrahydrofuran2×HCID 130669462-Methyl-3-hydroxy-4-mercaptomethyl-5-vinylpyridine

Product 1

HCID 130669512-Methyl-3-acetoxy-4-acetylthiomethyl-5-vinylpyridine

Procedure

A mixture of 680 mg. of acetic anhydride and 10 ml. of tetrahydrofuran was added slowly to 653 mg. of 2-methyl-3-hydroxy-4-mercaptomethyl-5-vinylpyridine in 20 ml. of tetrahydrofuran at 10° C. After stirring for one hour at room temperature, the mixture was evaporated to dryness. The residue was triturated with a mixture of 20 ml. of ethyl acetate and 20 ml. of water. The ethyl acetate was separated, dried over magnesium sulfate, and evaporated to dryness. The residue was recrystallized from cyclohexane to give 2-methyl-3-acetoxy-4-acetylthiomethyl-5-vinylpyridine, m.p. 72°-73° C. The same product is obtained by starting with the S-acetate product of Example 5.

Workup

  1. additionA mixture of 680 mg
  2. customat 10° C
  3. customthe mixture was evaporated to dryness
  4. customThe residue was triturated with a mixture of 20 ml
  5. customThe ethyl acetate was separated
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness
  8. customThe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-c2b00daa4f36416ea136113cc5892986
Source dataset
uspto-grants-1980_08
Patent number
US04217352

Reaction notes

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