153787-16-7 → Ethyl chroman-3-carboxylate

HRID 1446385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446385
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH2:4][CH:3]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]>[Pd].C(O)(=O)C>[O:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:2][CH:3]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:4]1

Komponenten

4

Edukt 1

HCID 67239220153787-16-7

Produkt 1

HCID 53408537Ethyl chroman-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 4-oxochromane-3-carboxylic acid, ethyl ester (4.0 g, 18 mmol) and 10% palladium on carbon (0.4 g) in 100 mL of acetic acid was degassed and filled with hydrogen using a balloon. After stirring at 70° C. overnight, the reaction mixture was filtered through CELITE diatomaceous earth, and the CELITE cake was washed with ethyl acetate (200 mL). The filtrate was washer with water (2×200 mL), dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): δ 7.2-7.0 (m, 2H), 6.84 (t, 1H), 6.74 (d, 1H), 4.36 (dd, 1H), 4.21-4.13 (m, 3H), 3.03 (m, 3H), 1.26 (t, 3H).

Aufarbeitung

  1. customwas degassed
  2. additionfilled with hydrogen using a balloon
  3. filtrationthe reaction mixture was filtered through CELITE diatomaceous earth
  4. washthe CELITE cake was washed with ethyl acetate (200 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-1a58fc77b5cb46c293db5f2016ceaaf3
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07667053B2

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