Hydrochloric Acid → 5-(4-Triisopropylsilanyloxyphenyl)selenophene-2-carbaldehyde

HRID 1873425Notes

Reaction equation

HRID 1873425 reaction equation
[CH:1]([Si:4]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[Se:13][CH:14]=[CH:15][CH:16]=2)=[CH:8][CH:7]=1)([CH3:3])[CH3:2].[Li]CCCC.[CH:28](N1CCOCC1)=[O:29].Cl>C(OCC)C.O>[CH:20]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:17]([CH3:19])[CH3:18])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[Se:13][C:14]([CH:28]=[O:29])=[CH:15][CH:16]=2)=[CH:8][CH:7]=1)([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 20417N-FormylmorpholineHCID 86644790Triisopropyl-(4-selenophen-2-ylphenoxy)silaneHCID 178418339Butyllithium

Product 1

HCID 866447915-(4-Triisopropylsilanyloxyphenyl)selenophene-2-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-70 °C

Procedure

11.0 g (27.9 mmol) of triisopropyl-(4-selenophen-2-ylphenoxy)silane are initially introduced in 200 ml of diethyl ether, and 20 ml (31.8 mmol, 15% soln. in hexane) of n-BuLi are metered in rapidly. The mixture is heated under reflux for 30 min and subsequently cooled to −70° C. 15.0 ml (0.15 mol) of N-formylmorpholine in 50 ml of diethyl ether are added, and the mixture is warmed to RT and stirred for 1 h. The mixture is added to water, and 2 N hydrochloric acid is added. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, toluene). 5-(4-Triisopropylsilanyloxyphenyl)selenophene-2-carbaldehyde is obtained as a red solid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 30 min
  3. temperaturethe mixture is warmed to RT
  4. additionis added
  5. customThe organic phase is separated off
  6. extractionthe aqueous phase is extracted with MTBE
  7. washThe combined organic phases are washed with sat. sodium chloride soln
  8. customand dried
  9. concentrationThe solution is concentrated to dryness
  10. customthe residue is purified by column chromatography (SiO2, toluene)

Sources & evidence

ORD record
ord-90e76adba8e34c3daa82867c50355409
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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