Piperidine → 3-(3-Fluoro-4-methoxy-phenylsulfanyl)-3-methyl-butyric acid

HRID 619608Notes

Reaction equation

[CH3:1][C:2]([CH3:7])=[CH:3][C:4]([OH:6])=[O:5].[F:8][C:9]1[CH:10]=[C:11]([SH:17])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16].N1CCCCC1>CCOC(C)=O>[F:8][C:9]1[CH:10]=[C:11]([S:17][C:2]([CH3:7])([CH3:1])[CH2:3][C:4]([OH:6])=[O:5])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

Conditions

Temperature: 105 °C

Procedure

A heavy-walled screw cap tube was charged with 3-methyl-2-butenoic acid (1.23 g, 12.33 mmol), 3-fluoro-4-methoxy thiophenol (Compound 200, 1.95 g, 12.33 mmol), and piperidine (314.8 mg, 3.70 mmol). This mixture was heated to 105° C. for 23 hours, cooled to room temperature and dissolved in EtOAc (100mL). 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 3.22 g of a clear yellow oil which was used in the next reaction without further purification. 1H NMR (300 MHz, CDCl3) δ: 7.32 (2H, m), 6.94 (1H, t, J=8.4 Hz), 3.92 (3H, s), 2.54 (2H, s), 1.41 (6H, s).

Workup

customA heavy-walled screw cap tube
temperaturecooled to room temperature
washThe resulting solution was washed with 1M aqueous HCl, H2O, and saturated aqueous NaCl
dry with materialbefore being dried over Na2SO4

Sources & evidence

ORD record: ord-61f98eb6c00e4b1b912fd8b5129f8fd8
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05958954

Reaction notes

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