Diethyl Ether → HCID 22119680, compound

HRID 1291977Notes

Reaction equation

HRID 1291977 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 26% 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 26% ethyl acetate-hexane

Sources & evidence

ORD record
ord-1177e02e08164c509780210fda3fa452
Source dataset
uspto-grants-1998_05
Patent number
US05756259

Reaction notes

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