Cinnamic Acid → 4-tert-butyl-10,10-dimethyl-3,6-dioxo-2,7-dioxa-4-aza-10-silaundec-1-yl (2E)-3-phenylacrylate

HRID 421578

Reaktionsgleichung

Reaktionsgleichung von HRID 421578
[C:1]([OH:11])(=[O:10])/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:30]([N:34]([C:45]([O:47][CH2:48]Cl)=[O:46])[CH2:35][C:36]([O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])=[O:37])([CH3:33])([CH3:32])[CH3:31]>CO>[C:4]1(/[CH:3]=[CH:2]/[C:1]([O:11][CH2:48][O:47][C:45](=[O:46])[N:34]([C:30]([CH3:32])([CH3:31])[CH3:33])[CH2:35][C:36](=[O:37])[O:38][CH2:39][CH2:40][Si:41]([CH3:42])([CH3:43])[CH3:44])=[O:10])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 444539Cinnamic AcidHCID 2723671Tetrabutylammonium HydroxideHCID 866110192-(Trimethylsilyl)ethyl 2-(tert-butyl((chloromethoxy)carbonyl)amino)-acetate

Produkt 1

HCID 588261794-tert-butyl-10,10-dimethyl-3,6-dioxo-2,7-dioxa-4-aza-10-silaundec-1-yl (2E)-3-phenylacrylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Trans-cinnamic acid (23.1 mmol) and 1.0 M tetrabutylammonium hydroxide (22.2 mmol) in methanol are stirred for one hour, and the methanol is removed. THF is added. To this solution is added 2-(trimethylsilyl)ethyl 2-(tert-butyl((chloromethoxy)carbonyl)amino)-acetate (18.5 mmol) and the mixture is stirred at room temperature for 24 hr. The solvent is removed and the residue is diluted with ether. The resulting solution is washed with water and brine. The organic layer is dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield 5.01 g (61%) MS (ESI) m/z 436.3.

Aufarbeitung

  1. customthe methanol is removed
  2. additionTHF is added
  3. customThe solvent is removed
  4. additionthe residue is diluted with ether
  5. washThe resulting solution is washed with water and brine
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield 5.01 g (61%)

Quellen und Nachweise

ORD-Eintrag
ord-43c9a01e833442d19214623c988353dc
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101590B2

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