Sodium methanethiolate → 1-(2-Hydroxyphenyl)-4-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol

HRID 1073873

Reaction equation

HRID 1073873 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=1)([OH:14])[CH:10]=[C:11]([CH3:13])C.[CH3:22][S-].[Na+]>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[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=1)([OH:14])[CH:10]=[CH:11][CH2:13][CH3:22]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 198956601-(2-Methoxyphenyl)-3-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol

Product 1

HCID 545243991-(2-Hydroxyphenyl)-4-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-olYield 66.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

7.13 g of 1-(2-methoxyphenyl)-3-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol were dissolved in 100 ml of dimethylformamide at room temperature and 5.29 g of sodium methanethiolate were added. After stirring at 120° C. for 2 hours the mixture was allowed to cool to room temperature and then evaporated. Water and ethyl acetate were added, and the organic phase was separated, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. There were obtained 4.53 g of 1-(2-hydroxyphenyl)-4-methyl-1-(3-methyl-2-pyridyl)-2-buten-1-ol in the form of an oil.

Workup

  1. temperatureto cool to room temperature
  2. customevaporated
  3. additionWater and ethyl acetate were added
  4. customthe organic phase was separated
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-2de101ede6b94f8b82533aa62d05aad9
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Linked notes

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