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

HRID 1588423

반응식

HRID 1588423 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 769Bicarbonate Ion용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c095b32270de4527b7c200b864be4b09
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05221760

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