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

HRID 918792Notes

Reaction equation

HRID 918792 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

Conditions

Temperature
10 °C

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 10° C. for 32 hours, cooled to room temperature and dissolved in EtOAc (700 mL). The resulting solution was washed with 1 M 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 as pale-yellow crystals by washing the crystalline solid with pentane. (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 is (3H, s), 2.54 (2H, s), 1.40 (6H, s).

Workup

  1. customA heavy-walled screw cap tube
  2. temperaturecooled to room temperature
  3. washThe resulting solution was washed with 1 M 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-6f881f9429a54312a52acf83e37b6e6a
Source dataset
uspto-grants-2016_03
Patent number
US09271946B2

Reaction notes

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