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

Reaction equation

HRID 421578 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-43c9a01e833442d19214623c988353dc
Source dataset
uspto-grants-2012_01
Patent number
US08101590B2

Linked notes

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