Diethyl Ether → HCID 20136893, compound

HRID 1253146Notes

Reaction equation

HRID 1253146 reaction equation
[CH3:1][SiH:2](Cl)[CH3:3].[C:5]([O:9]CCO)(=[O:8])C=C.C(N([CH2:18][CH3:19])CC)C.[CH2:20]([O:22]CC)[CH3:21]>>[CH2:20]([O:22][C:18](=[CH2:19])[C:5]([O-:9])=[O:8])[CH3:21].[CH2:20]([O:22][C:18](=[CH2:19])[C:5]([O-:9])=[O:8])[CH3:21].[CH3:1][Si+2:2][CH3:3]

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 131652-Hydroxyethyl acrylateHCID 66108Chlorodimethylsilane

Product 1

HCID 20136893HCID 20136893, compound

Procedure

Dimethylsilylchloride (6.1 g; 0.047M) was added slowly to an ice cooled mixture of 2-hydroxyethyl acrylate (11 g; 0.0974M), triethylamine (9.6 g; 0.0947M) and dry diethyl ether (100 ml). The mixture was then refluxed for 2 hours and cooled. The triethylamine hydrochloride precipitate was filtered off and the solvent removed from the filtrate to give 6.6 g (81% of theory) of the product. An attempt to purify the product by distillation was unsuccessful because the product polymerized on heating. Infrared and NMR spectral analysis of the product confirmed it as the title compound and the results are summarised in Table S2 below.

Workup

  1. temperaturecooled
  2. temperatureThe mixture was then refluxed for 2 hours
  3. temperaturecooled
  4. filtrationThe triethylamine hydrochloride precipitate was filtered off
  5. customthe solvent removed from the filtrate
  6. customto give 6.6 g (81% of theory) of the product
  7. customAn attempt to purify the product
  8. distillationby distillation
  9. custompolymerized
  10. temperatureon heating

Sources & evidence

ORD record
ord-b583a9c485354605a13f1501c5475385
Source dataset
uspto-grants-1988_05
Patent number
US04748087

Reaction notes

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