Triethylamine → 4-Formylcinnamic acid tert-butyl ester

HRID 556280

反応式

HRID 556280 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+].[C:22]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])(=[O:25])[CH:23]=[CH2:24]>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:27]([O:26][C:22](=[O:25])[CH:23]=[CH:24][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)([CH3:30])([CH3:29])[CH3:28]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 707414-BromobenzaldehydeHCID 516892Sodium Bicarbonate

生成物 1

HCID 541476044-Formylcinnamic acid tert-butyl ester収率 70%

試薬・触媒・溶媒 4

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒2 回HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A solution of 4-bromo benzaldehyde (2 g, 10.8 mmol) in DMF (50 ml) and triethylamine (3.4 ml, 27 mmol) was degassed flushing N2 for 30 min. PPh3 (141 mg, 0.54 mmol), Pd(OAc)2 (48.4 mg, 0.21 mmol), NaHCO3 (1.84 g, 21.6 mmol) and tert-butyl acrylate (1.58 ml, 10.8 mmol) were added and the resulting mixture was heated to reflux for 3 h. Additional Pd(OAc)2 (24 mg) was added and the mixture was heated to 100° C. for 1 h. The solution was diluted with H2O and extracted with Et2O. The organic layer was dried over Na2SO4 and the solvent was evaporated under vacuo to give the crude product that was triturated in isopropyl ether to give 1.6 g of 3-(4-formyl-phenyl)-acrylic acid tert-butyl ester.

後処理

  1. customflushing N2 for 30 min
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 3 h
  4. extractionextracted with Et2O
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe solvent was evaporated under vacuo
  7. customto give the crude product that
  8. customwas triturated in isopropyl ether

出典と根拠

ORDレコード
ord-4c0e5a8c3bc640fb8024f6cba150baa7
出典データセット
uspto-grants-2011_11
特許番号
US08058273B2

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