Propanediol → HCID 86757251, Verbindung

HRID 650619

Reaktionsgleichung

Reaktionsgleichung von HRID 650619
[C:1]([C:9]1[CH:10]=[C:11]([C@H:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20](O)([OH:23])[CH2:21][CH3:22]>>[C:1]([C:9]1[CH:10]=[C:11]([C@H:15]([CH3:19])[C:16]([O:18][CH2:22][CH2:21][CH2:20][OH:23])=[O:17])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 134919PropanediolHCID 667550Dexketoprofen

Produkt 1

HCID 86757251HCID 86757251, VerbindungAusbeute 56,1 %

Versuchsvorschrift

Compound 18 was synthesized as described above for compound 10 from (S)-(+)-3-benzoyl-α-methylbenzeneacetic acid (ketoprofen, 17) (3.8 g, 15 mmol) and propanediol (9) (5.7 g, 75 mmol). The compound was purified by flash chromatography on a silica gel column using 200:1 CH2Cl2—MeOH as the eluent to give 2.63 g (56%) of the compound 18 as a colorless oil; 1H NMR (CDCl3) δ1.54 (d, 3H), 1.82 (m, 2H), 1.82-1.82 (b, 1H, ex D2O), 3.58 (m, 2H), 3.79-3.83 (q, 1H), 4.25 (m, 2H), 7.42-7.80 (m, 9H); MS (ES) m/z 313.1 (M+H)+ (C19H21O4 requires 313.3).

Aufarbeitung

  1. customCompound 18 was synthesized
  2. customThe compound was purified by flash chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-adc936e0d5c44c759f0e3426eebedc64
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06274627B1

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