Hydrochloric Acid → 1-(2-Hydroxyphenyl)-3-methyl-1-(2-pyridyl)-2-buten-1-ol

HRID 892502Notes

Reaction equation

HRID 892502 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([OH:14])[CH:10]=[C:11]([CH3:13])[CH3:12].C[S-].[Na+].Cl>CN(C)C=O>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)([OH:14])[CH:10]=[C:11]([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 198955961-(2-Methoxyphenyl)-3-methyl-1-(2-pyridyl)-2-buten-1-ol

Product 1

HCID 198956121-(2-Hydroxyphenyl)-3-methyl-1-(2-pyridyl)-2-buten-1-olYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

36.6 g of 1-(2-methoxyphenyl)-3-methyl-1-(2-pyridyl)- 2-buten-1-ol were heated at 70° C. in 200 ml of dimethylformamide with 28.6 g of sodium methanethiolate. After 10 hours the mixture was allowed to cool to room temperature, poured into dilute hydrochloric acid and extracted with ethyl acetate. The organic extract was dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate for the elution to give 28.5 g of 1-(2-hydroxyphenyl)-3-methyl-1(2-pyridyl)-2-buten-1-ol in the form of an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-714bfb56d37246be99e6593fa9ac8642
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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