Diethyl Ether → HCID 22119680, compound

HRID 725170Notes

Reaction equation

HRID 725170 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:12][CH3:13])[C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1.C(N(CC)CC)C.Cl[Si:22]([CH3:25])([CH3:24])[CH3:23].C(OCC)C>O1CCCC1>[CH3:23][Si:22]([CH3:25])([CH3:24])[O:1][CH2:2][CH2:3][N:4]([CH2:12][CH3:13])[C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 11150468HCID 11150468, compound

Product 1

HCID 22119680HCID 22119680, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 14.5 g, that is 50 mmole of 4-[(2-hydroxyethyl)ethylamino]iodobenzene and 6.0 g, that is 60 mmole triethylamine, from Aldrich Chemical Co. in 90 ml tetrahydrofuran ("THF") was stirred in an ice-water bath under nitrogen. Next, 5.5 g, 51 mmole chlorotrimethylsilane, from Aldrich Chemical Co. was added slowly while maintaining the reaction temperature below 10° C. The mixture was stirred for 30 minutes then warmed to room temperature for 1 hour. Ethyl ether was added and extracted with brine. The organic layer was separated and dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, the residue was flash column chromatographed on silica gel with 2% ethyl acetate-hexane to give 16.63 g of a clear viscous oil at a 92% yield.

Workup

  1. additionwas added slowly
  2. temperaturewhile maintaining the reaction temperature below 10° C
  3. extractionextracted with brine
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removing the solvent under reduced pressure
  7. customchromatographed on silica gel with 2% ethyl acetate-hexane

Sources & evidence

ORD record
ord-a8ee92dd371c4b87965e1ac13f14e413
Source dataset
uspto-grants-1998_01
Patent number
US05705570

Reaction notes

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