Piperidine → Butanoic acid, 3-[(4-methoxyphenyl)thio]-3-methyl-

HRID 324249Notes

Reaction equation

HRID 324249 reaction equation
[CH3:1][C:2]([CH3:7])=[CH:3][C:4]([OH:6])=[O:5].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1.N1CCCCC1>CCOC(C)=O>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:2]([CH3:7])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 109313-Methyl-2-butenoic acidHCID 127654-Methoxybenzenethiol

Product 1

HCID 10171427Butanoic acid, 3-[(4-methoxyphenyl)thio]-3-methyl-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A heavy-walled screw cap tube was charged with 3-methyl-2-butenoic acid (13.86 g. 138.4 mmol), 4-methoxy thiophenol (20.0 g. 138.4 mmol), and piperidine (3.45 g. 41.6 mmol). This mixture was heated to 05° C. for 32 hours, cooled to room temperature and dissolved in EtOAc (700 mL). The resulting solution was washed with 1M aqueous HCl, H2O, and saturated aqueous NaCl before being dried over Na2SO4. Concentration of the dry solution under reduced pressure afforded an oil which upon standing in the freezer provided a crystalline solid. 3-(4-methoxy-phenylsulfanyl)3-methyl-butyric acid was isolated using a pentane wash as pale-yellow crystals (27.33 g. 82%). 1H NMR (300 MHz, CDCl3 δ: 7.48 (2H, d, J=9.0 Hz), 6.89 (2H, d, J=8.9 Hz), 3.83 (3H, s), 2.54 (2H, s).1.40 (6H, s).

Workup

  1. customA heavy-walled screw cap tube
  2. temperatureThis mixture was heated to 05° C
  3. washThe resulting solution was washed with 1M aqueous HCl, H2O, and saturated aqueous NaCl
  4. dry with materialbefore being dried over Na2SO4
  5. customConcentration of the dry solution under reduced pressure afforded an oil which
  6. customprovided a crystalline solid

Sources & evidence

ORD record
ord-2e51f15681e7448f993d6c5ca4e573d0
Source dataset
uspto-grants-2001_04
Patent number
US06218128B1

Reaction notes

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