Triphenylphosphine → HCID 22010469, Verbindung

HRID 322964

Reaktionsgleichung

Reaktionsgleichung von HRID 322964
N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH:34][C:35]1[CH:40]=[C:39]([O:41][CH2:42][C:43]2[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=2)[CH:38]=[CH:37][C:36]=1[C:49](=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1.O[CH:58]([C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][C:69]=1[CH3:74])[CH2:59][CH2:60][C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62]>O1CCCC1>[C:49]([C:36]1[CH:37]=[CH:38][C:39]([O:41][CH2:42][C:43]2[CH:44]=[N:45][CH:46]=[CH:47][CH:48]=2)=[CH:40][C:35]=1[O:34][CH:58]([C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][C:69]=1[CH3:74])[CH2:59][CH2:60][C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])(=[O:56])[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 22010446HCID 22010446, VerbindungHCID 220104602'-Hydroxy-4'-(pyridin-3-ylmethoxy)benzophenone

Produkt 1

HCID 22010469HCID 22010469, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Diisopropyl azodicarboxylate (6.45 mL) is added dropwise to a stirred, cooled (0° C.) solution of triphenylphosphine (8.6 g) in dry tetrahydrofuran (60 mL). After a further 30 minutes, a solution of 2′-hydroxy-4′-(pyridin-3-ylmethoxy)benzophenone (5 g) and tert-butyl 4-hydroxy-4-(2-methylphenyl)butanoate, thought to be the (S)-enantiomer, (5.13 g) in dry tetrahydrofuran (60 mL) is added dropwise over 25 minutes and stirring continued for a further 3 hours at °C. The reaction is allowed to warm to ambient temperature overnight before being concentrated under vacuo. The resultant oil is purified by flash chromatography on silica eluting with a mixture of dichloromethane and ethyl acetate (9:1 v/v). Fractions homogeneous in the required product are combined and concentrated under reduced pressure to give t-butyl 4-[2-benzoyl-5-(pyridin-3-ylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate, thought to be the (R)-enantiomer, as a colourless oil (8.66 g).

Aufarbeitung

  1. additionis added dropwise over 25 minutes
  2. waitcontinued for a further 3 hours at °C
  3. concentrationbefore being concentrated under vacuo
  4. customThe resultant oil is purified by flash chromatography on silica eluting with a mixture of dichloromethane and ethyl acetate (9:1 v/v)
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b004517b0d8a45d8b9785a858c9f66a8
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211234B1

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