Dimethylformamide dimethyl acetal → HCID 57732419, Verbindung

HRID 1365066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1365066
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>>[CH3:21][N:22]([CH3:24])/[CH:23]=[CH:9]/[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH:11]([OH:18])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:4]=1)=[O:10]

Komponenten

3

Edukt 2

HCID 78373Dimethylformamide dimethyl acetalHCID 577324311-[4-Fluoro-3-(hydroxyphenylmethyl)phenyl]ethanone

Produkt 1

HCID 57732419HCID 57732419, Verbindung

Versuchsvorschrift

A round-bottomed flask was charged with 1-{4-fluoro-3-[hydroxy(phenyl)methyl]phenyl}ethanone (140 mg) and dimethylformamide dimethylacetal (4 mL). The mixture was heated to reflux for 18 h then concentrated to dryness. The residue was taken up in minimal methylene chloride then added to rapidly stirring diethyl ether to induce a solid. The solids were collected on filter and washed with diethyl ether to provide (2E)-3-(dimethylamino)-1-{4-fluoro-3-[hydroxy(phenyl)methyl]phenyl}-2-propen-1-one as a white powder (60 mg). 8.09 (dd, 1H), 7.82 (m, 1H), 7.69 (d, 1H), 7.31 (m, 4H), 7.21 (m, 1H), 7.14 (dd, 1H), 6.06 (d, 1H), 5.94 (d, 1H), 5.75 (d, 1H), 3.14 (s, 3H), 2.88 (s, 3H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 h
  3. concentrationthen concentrated to dryness
  4. additionthen added to rapidly stirring diethyl ether
  5. customThe solids were collected
  6. filtrationon filter
  7. washwashed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-739cc7860f1b4969ac9766ee7c136ecf
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888503B2

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