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Methanol → HCID 58822697, Verbindung

HRID 459141
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 459141
C([O:3][C:4](=[O:19])[C@@H:5]([O:17][CH3:18])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:16])[CH2:14]Br)=[CH:9][CH:8]=1)C.[C:20]1([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])([O-])=O.[K+].[K+].CO>C(#N)C.[OH-].[Na+].[Cl-].[Na+].O>[C:26]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:27]=[CH:28][C:29]([O:32][CH2:14][C:13]([C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C@H:5]([O:17][CH3:18])[C:4]([OH:3])=[O:19])=[CH:12][CH:11]=2)=[O:16])=[CH:30][CH:31]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 887Methanol2×HCID 71034-HydroxybiphenylHCID 11430Potassium CarbonateHCID 58822842HCID 58822842, Verbindung

Produkt 1

HCID 58822697HCID 58822697, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6342
Acetonitrile
Lösungsmittel
HCID 14798Sodium HydroxideLösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The title compound was prepared from a solution of (2S)-3-[4-(2-Bromo-acetyl)-phenyl]-2-methoxy-propionic acid ethyl ester (25 mg, 0.076 mmol) in acetonitrile (5 ml). 4-phenylphenol (29 mg, 0.152 mmol) and K2CO3 (31,5 mg, 0.23 mmol) were added. The solution was stirred for 30 min at 80° C. and then cooled to room temperature. The mixture was concentrated to dryness under vacuum and chromatographed in silica gel (hexanes/Ethyl ether 8:2 to 7:3). Fractions corresponding to the coupled compound were collected (Rf0.27) and concentrated to dryness. The mixture thus obtained was dissolved in 4 mL of NaOH 1N and 12 mL of Methanol and stirred at room temperature until TLC indicates the disappearance of starting material. The methanol was eliminated under vacuum and the aqueous solution diluted with 20 mL of brine and washed with diethyl ether (3×15 mL). The aqueous phase was acidulated with HCl 1N (until pH 3); extracted with ethyl acetate (3×15 mL) and the organic layer dried (MgSO4) and concentrated under vacuum. Obtained a colorless oil (9.6 mg, 32%). 1H-NMR (200.15 MHz; CDCl3): δ 7.96 (d, 2H, J=8.4), 7.55–7.23 (m, 9H), 6.99 (d, 2H, J=8.8), 5.26 (s, 2H), 4.03 (dd, 1H, J=7.3, 5.6), 3.39 (s, 3H), 3.22 (dd, 1H, J=14.3, 5.5), 3.03 (dd, 1H, J=14.3, 7.2).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. concentrationThe mixture was concentrated to dryness under vacuum
  3. customchromatographed in silica gel (hexanes/Ethyl ether 8:2 to 7:3)
  4. customFractions corresponding to the coupled compound were collected (Rf0.27)
  5. concentrationconcentrated to dryness
  6. customThe mixture thus obtained
  7. washwashed with diethyl ether (3×15 mL)
  8. extractionextracted with ethyl acetate (3×15 mL)
  9. dry with materialthe organic layer dried (MgSO4)
  10. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-dec2e16e7b6f4968ae2555146c9590b2
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07192982B2

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