StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sodium Iodide → 4-Methylpentyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 57219
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 57219
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Br[CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CN(C)C=O.CCOC(C)=O.[Cl-].[Na+].O.O>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:25][CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 69385Pentane, 1-bromo-4-methyl-HCID 1151755-(Tetradecyloxy)-2-furoic acid2×

Produkt 1

HCID 668698124-Methylpentyl 5-(tetradecyloxy)furan-2-carboxylateAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a vigorously stirred suspension of 5-(tetradecyloxy)furan-2-carboxylic acid (0.162 g, 0.5 mmol) in 10 mL of N,N-dimethylformamide was added 1-bromo-4-methylpentane (0.247 g, 1.5 mmol), cesium carbonate (0.243 g, 0.75 mmol) and sodium iodide (˜20 mg). The suspension appeared to go into solution briefly, and then a very finely dispersed white precipitate was observed. The reaction was allowed to stir for 12 hrs at which time HPLC analysis of the reaction solution indicated complete conversion of TOFA to a less polar product. The suspension was diluted with EtOAc (40 mL), brine (20 mL) and water (20 mL). The phases were separated and the organic phase was washed with water (20 mL) and brine (20 mL) and then dried and concentrated. The resulting crude material was purified by flash chromatography eluting with 0-20% EtOAc in hexanes to yield 0.127 g (62%) of the title compound. 1H NMR (300 MHz, CDCl3) δ: 7.15 (d, 1H), 5.30 (d, 1H), 4.22 (t, 2H), 4.10 (t, 2H), 1.18-1.80 (m, 29H), 0.89 (t, 9H).

Aufarbeitung

  1. customThe phases were separated
  2. washthe organic phase was washed with water (20 mL) and brine (20 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting crude material was purified by flash chromatography
  6. washeluting with 0-20% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-06c8b30c5e0f4d0090984b9d5fe78529
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09434718B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion