Ethanol → 16-Fluoro-4-thia-hexadecanoic acid

HRID 279426Notes

Reaction equation

HRID 279426 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14][CH2:15][CH2:16][C:17]([O:19]C)=[O:18].[F-:21].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[K+].C(O)C>CCCCCC.CCOCC.C(O)(=O)C>[F:21][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][S:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 14797Potassium HydroxideHCID 2724141Tetrabutylammonium FluorideHCID 22625147Methyl 16-iodo-4-thia-hexadecanoate

Product 1

HCID 2262515116-Fluoro-4-thia-hexadecanoic acidYield 34.2%

Reagents, catalysts & solvents 1

HCID 21924843Hexane ether acetic acidSolvent

Procedure

Fluorination of 1 (0.2 g, 0.5 mmol) was performed by addition of tetrabutylammonium fluoride (TBAF) (4 mmol as 1M THF solution). The mixture was allowed to react at room temperature for 20 h. The resulting fluoro-ester was hydrolyzed by addition of 1 ml 1 N KOH and 1 ml ethanol for 2 h at room temperature. The product 2 (0.05 g, 34% yield) was isolated by column chromatography (hexane/ether/acetic acid 3:1:0.1) and recrystallized in hexane, TLC (hexane/ether/acetic acid 3:1:0.1) Rf=0.25. Melting point=59° C., 1H-NMR δ1.4 (m, 20H, CH2), 2.55 (t, 2H, C(2)H2), 2.65 (t, 2H, C(5)H2), 2.80 (t, 2H, C(3)H2), 4.44 (dt, 2H, C(16)H2JHH=6.2 Hz).

Workup

  1. customto react at room temperature for 20 h

Sources & evidence

ORD record
ord-d67843a207174568a87b70b3bf694593
Source dataset
uspto-grants-2002_03
Patent number
US06362352B1

Reaction notes

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