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

HRID 1588423Notes

Reaction equation

HRID 1588423 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 769Bicarbonate IonSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c095b32270de4527b7c200b864be4b09
Source dataset
uspto-grants-1993_06
Patent number
US05221760

Reaction notes

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