Aluminum(III) Chloride → (R)-6-fluoro-3-(3-fluorophenyl)-2-(1-hydroxyethyl)-4H-chromen-4-one

HRID 626296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626296
C([O:8][C@@H:9]([C:11]1[O:12][C:13]2[C:18]([C:19](=[O:28])[C:20]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)=[CH:17][C:16]([F:29])=[CH:15][CH:14]=2)[CH3:10])C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[F:29][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[O:12][C:11]([C@H:9]([OH:8])[CH3:10])=[C:20]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)[C:19]2=[O:28]

Komponenten

4

Edukt 2

HCID 6451240Aluminum(III) ChlorideHCID 117867472(R)-2-(1-(benzyloxy)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one

Produkt 1

HCID 71816279(R)-6-fluoro-3-(3-fluorophenyl)-2-(1-hydroxyethyl)-4H-chromen-4-oneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To (R)-2-(1-(benzyloxy)ethyl)-6-fluoro-3-(3-fluorophenyl)-4H-chromen-4-one (10.5 g, 26.69 mmol) in Dichloromethane (110 ml) cooled to 0° C., anhydrous Aluminium chloride (5.35 g, 40.03 mmol) was added portion wise and stirred for 1 h and then at RT for 2 h. The reaction mixture was quenched with dilute aq. HCl (10 ml), extracted with Dichloromethane (2×50 ml). The organic layer was dried over sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as off-white solid (6.5 g, 81%). 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.86 (dd, J=8.3, 3.0 Hz, 1H), 7.56 (dd, J=9.2, 4.2 Hz, 1H), 7.45 (m, 2H), 7.12-6.99 (m, 3H), 4.76 (q, J=6.6 Hz, 1H), 1.55 (d, J=6.6 Hz, 3H). Mass: 303.2 (M++1). Purity: 99.78%. [α]25D 0.287 (c=1, CHCl3). Enantiomeric excess: 97.74%, enriched in the late eluting isomer (retention time: 10.93 min.) as determined by HPLC on a chiralpak AD-H column.

Aufarbeitung

  1. waitat RT for 2 h
  2. customThe reaction mixture was quenched with dilute aq. HCl (10 ml)
  3. extractionextracted with Dichloromethane (2×50 ml)
  4. dry with materialThe organic layer was dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-43e921719ab0413895201e2b8c2ef981
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309216B2

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