Tetrahydrofuran → Benzoic acid, 4-hexyl-, methyl ester

HRID 1795377

Reaktionsgleichung

Reaktionsgleichung von HRID 1795377
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7](OS(C(F)(F)F)(=O)=O)=[CH:6][CH:5]=1.C1COCC1.CN1CCCC1=O.[CH2:31]([Mg]Br)[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]>CCOCC>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 13387N-methyl-2-pyrrolidoneHCID 5315090Methyl 4-(((trifluoromethyl)sulfonyl)oxy)benzoateHCID 178444609HCID 178444609, Verbindung

Produkt 1

HCID 591633Benzoic acid, 4-hexyl-, methyl esterAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A flame-dried two-necked flask is charged under argon with 4-(trifluoromethylsulfonyloxy)benzoic acid methyl ester (760 mg, 2.66 mmol), Fe(acac)3 (47 mg, 0.13 mmol), THF (30 mL) and N-methylpyrrolidone (NMP, 1.7 mL). A solution of n-hexylmagnesium bromide (2M in Et2O, 1.7 mL, 3.4 mmol) is added via syringe to the resulting red solution, causing an immediate color change to dark brown and finally to violet. The resulting mixture is stirred for 5 min, the reaction is diluted with Et2O and is carefully quenched upon addition of aq. HCl (1M, ca. 10 mL). Work-up followed by flash chromatography of the crude product as described above provides 4-hexylbenzoic acid methyl ester as a colorless syrup (540 mg, 93%). The spectroscopic and analytical data are identical to those compiled above.

Aufarbeitung

  1. customis carefully quenched upon addition of aq. HCl (1M, ca. 10 mL)

Quellen und Nachweise

ORD-Eintrag
ord-247077bc74b74d10a2c4b0718a7f4454
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026478B2

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