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

反応式

HRID 421578 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-43c9a01e833442d19214623c988353dc
出典データセット
uspto-grants-2012_01
特許番号
US08101590B2

関連ノート

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