Chlorotrimethylsilane → 3-(4-Methoxycarbonylphenyl)-1-trimethylsilyloxy-1-propene

HRID 1588423ノート

反応式

HRID 1588423 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH:13]=[O:14])=[CH:7][CH:6]=1)=[O:4].[CH3:15][Si:16]([CH3:19])([CH3:18])Cl.C(N(CC)CC)C>CN(C)C=O.C(=O)(O)[O-]>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]=[CH:13][O:14][Si:16]([CH3:19])([CH3:18])[CH3:15])=[CH:7][CH:6]=1)=[O:4]

参加物

6

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 10104031Methyl 4-(3-oxopropyl)benzoate

生成物 1

HCID 543828473-(4-Methoxycarbonylphenyl)-1-trimethylsilyloxy-1-propene

試薬・触媒・溶媒 2

HCID 769Bicarbonate Ion溶媒HCID 6228Dimethylformamide溶媒

実験手順

9.61 g (50 mmol) 3-(4-Methoxycarbonylphenyl)propanal are dissolved, together with 8.3 ml (68 mmol) of trimethylchlorosilane and 18.1 ml (0.13 mol) of triethylamine, in 15 ml of absolute dimethyl formamide and the solution is heated under reflux for 2 hours under nitrogen. After cooling, the reaction mixture is diluted with a saturated bicarbonate solution and extracted with petroleum ether. The organic phase is washed 3 times with a saturated bicarbonate solution, dried with sodium sulphate and concentrated by evaporation. The residue is distilled under a high vacuum (distillation apparatus silylated). 11.06 g of a pale yellow, oily product are thus obtained in the form of a mixture of the cis- and trans-isomers.

後処理

  1. temperaturethe solution is heated
  2. temperatureunder reflux for 2 hours under nitrogen
  3. temperatureAfter cooling
  4. extractionextracted with petroleum ether
  5. washThe organic phase is washed 3 times with a saturated bicarbonate solution
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated by evaporation
  8. distillationThe residue is distilled under a high vacuum (distillation apparatus silylated)
  9. custom11.06 g of a pale yellow, oily product are thus obtained in the form of a mixture of the cis- and trans-isomers

出典と根拠

ORDレコード
ord-c095b32270de4527b7c200b864be4b09
出典データセット
uspto-grants-1993_06
特許番号
US05221760

反応ノート

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