9-Decenoic acid → But-3-en-1-yl dec-9-enoate

HRID 62557

Reaktionsgleichung

Reaktionsgleichung von HRID 62557
[C:1]([OH:12])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10].[CH2:13](O)[CH2:14][CH:15]=[CH2:16]>>[C:1]([O:12][CH2:16][CH2:15][CH:14]=[CH2:13])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH2:10]

Komponenten

3

Edukt 2

HCID 617439-Decenoic acidHCID 693893-Buten-1-ol

Produkt 1

HCID 86674987But-3-en-1-yl dec-9-enoate

Versuchsvorschrift

Following the aforementioned procedure, diene was prepared from dec-9-enoic acid and but-3-en-1-ol. The resulting yellow oil was purified by silica gel chromatography (30:1 hexanes: diethyl ether) to afford the desired product as a colorless oil. IR (neat): 3077 (m), 2927 (s), 2855 (s), 1737 (s), 1641 (m), 1458 (m), 1418 (m), 1353 (m), 1243 (s), 1170 (s), 1115 (m), 992 (s), 912 (s), 725 (m), 635 (m); 1H NMR (400 MHz, CDCl3): δ 5.86-5.74 (2H, m), 5.14-4.91 (4H, m), 4.12 (2H, t, J=6.8 Hz), 2.38 (2H, ddt, J=13.6, 6.8, 1.4 Hz), 2.29 (2H, t, J=7.6 Hz), 2.06-2.01 (2H, m), 1.63-1.59 (2H, m), 1.39-1.26 (8H, m); 13C NMR (100 MHz, CDCl3): δ 174.0, 139.3, 134.2, 117.3, 114.3, 63.4, 34.5, 33.9, 33.3, 29.2, 29.2, 29.1, 29.0, 25.1; HRMS (ESI+) [M+H]+ calcd for C14H25O2: 225.1855. found: 225.1855.

Aufarbeitung

  1. customThe resulting yellow oil was purified by silica gel chromatography (30:1 hexanes: diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-e946fc37bec74913a964dbd8eb58e268
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446394B2

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