Cinnamaldehyde → HCID 69747839, Verbindung

HRID 497479

Reaktionsgleichung

Reaktionsgleichung von HRID 497479
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:37])[CH2:15][CH2:16][CH2:17][CH2:18][O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C[C@H]2N(C[C@H]3[C@@H]4CCCCN4C[C@@H]2C3)CC1.[CH:55](=[O:64])/[CH:56]=[CH:57]/[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:37])[C@H:15]([CH2:16][CH2:17][CH2:18][O:19][Si:20]([C:33]([CH3:34])([CH3:36])[CH3:35])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C@H:55]([OH:64])[CH:56]=[CH:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 637511CinnamaldehydeHCID 644020SparteineHCID 59094988HCID 59094988, Verbindung

Produkt 1

HCID 69747839HCID 69747839, VerbindungAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirring solution of (R)-4-benzyl-3-[5-(tert-butyl-diphenyl-silanyloxy)-pentanoyl]-oxazolidin-2-one (1.64 g, 3.19 mmol) in dry methylene chloride (15.9 mL) in a flame dried round bottom flask under N2 at 0° C. was added titanium(IV) chloride (386 μL, 3.51 mmol). After 5 min, (−)-sparteine (1.83 mL, 7.97 mmol) was added. After 20 min, trans-cinnamaldehyde (442 μL, 3.51 mmol) was added dropwise to the purple suspension, and the resulting pale green-yellow solution was stirred for 1 h. The reaction was quenched by the addition of 50% saturated ammonium chloride (50 mL), diluted with water (100 mL), and then extracted with methylene chloride (3×30 mL). The organic layers were combined, washed with brine, dried over sodium sulfate, and concentrated in vacuo to a colorless oil. The oil was purified by flash chromatography (SiO2, 15-30% ethyl acetate in hexanes) to yield 1.72 g (83.1%) of the desired product as a white solid. MS (APCI), m+/z: (M+H)+=648.

Aufarbeitung

  1. waitAfter 20 min
  2. customThe reaction was quenched by the addition of 50% saturated ammonium chloride (50 mL)
  3. additiondiluted with water (100 mL)
  4. extractionextracted with methylene chloride (3×30 mL)
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo to a colorless oil
  8. customThe oil was purified by flash chromatography (SiO2, 15-30% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-906f29d688e64af9acd4ae62ff716c69
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949546B2

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