2-Phenylethanol → 7-(2-phenyl)ethoxyl-2-oxo-2H-1-benzopyran-3-carboxylic acid methyl ester

HRID 272802Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272802
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:16])[O:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([OH:15])[CH:9]=2)=[O:4].[C:17]1([CH2:23][CH2:24]O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:16])[O:7][C:8]2[CH:9]=[C:10]([O:15][CH2:24][CH2:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=[CH:12][C:13]=2[CH:14]=1)=[O:4]

Komponenten

6

Edukt 4

HCID 60542-PhenylethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5416969Methyl 7-hydroxy-2-oxo-2H-1-benzopyran-3-carboxylate

Produkt 1

HCID 100876097-(2-phenyl)ethoxyl-2-oxo-2H-1-benzopyran-3-carboxylic acid methyl esterAusbeute 46,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

7-hydroxyl-3-coumarin carboxylic acid methyl ester (0.6g, 3 mmol) and 2-phenyl ethanol (0.36 mL, 3 mmol) are dissolved in anhydrous tetrahydrofuran (60 mL). Triphenylphosphine (1.2 g, 4.5 mmol) is added, and diethyl azodicarboxylate (0.72 mL, 4.5 mmol) is added dropwise and slowly at 0° C. The resulting solution is stirred for 24 hours at room temperature. After the solvent was removed under reduced pressure, the residue is diluted with methanol and a white solid is separated out. The solid is recrystallized with methanol to give 0.45 g of the captioned compound, yield: 46.3%. m.p. 100-101° C. 1H NMR(CDCl3): δ=3.12(t, J=6.8 Hz, 2H), 3.92(s, 3H), 4.14(t, J=7.1 Hz, 2H), 6.79(d, J=2.4 Hz, 1H), 6.88(dd, J=2.4 Hz, 8.8 Hz, 1H), 7.21-7.35(m, 5H), 7.47(d, J=8.7 Hz, 1H), 8.50(s, 1H); Element Anyalysis, C19H16O5 (324): Calculated C, 70.37; H, 4.94. Found C, 70.25; H, 4.93; IR(KBr) :3045.1, 2952.5, 1751.1, 1693.2, 1610.3, 1554.4, 1506.2, 1436.7, 1375, 1307.5, 1222.7, 1114.7, 1018.2, 835, 749.5, 738.6, 700, 594 cm−1; EI-MS(m/z): 324(24, M+), 105(100).

Aufarbeitung

  1. customAfter the solvent was removed under reduced pressure
  2. additionthe residue is diluted with methanol
  3. customa white solid is separated out
  4. customThe solid is recrystallized with methanol

Quellen und Nachweise

ORD-Eintrag
ord-cf618d31fbd34afb8600c9cbbdb9b26e
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456205B2

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