Diethyl Ether → HCID 22119680, compound

HRID 581177Notes

Reaction equation

HRID 581177 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-7b04277924e947469b2a7437dbf88e70
Source dataset
uspto-grants-1999_07
Patent number
US05919868

Reaction notes

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