2-Iodophenol → HCID 58488432, compound

HRID 1510071Notes

Reaction equation

HRID 1510071 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH3:9][O:10][CH2:11][CH2:12][CH2:13]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:13][CH2:12][CH2:11][O:10][CH3:9]

Participants

6

Reactant 4

HCID 107842-IodophenolHCID 11776TriphenylphosphineHCID 741163-Methoxy-1-propanolHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 58488432HCID 58488432, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-iodophenol (3.00 g, 13.6 mmol), 3-methoxy-1-propanol (1.57 ml, 16.4 mmol) and triphenylphosphine (4.29 g, 16.4 mmol) in THF (15 ml) was added dropwise diisopropyl azodicarboxylate (3.22 ml, 16.4 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was quenched with water and extracted with EA. The organic layer was separated, dried over sodium sulfate, filtered, and evaporated under reduced pressure: The residue was purified by silica gel chromatography (EA/HEP 1:5). 4.00 g of the title compound were obtained.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EA
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (EA/HEP 1:5)

Sources & evidence

ORD record
ord-3e4d96ad4df742d7bd64b58191e135b5
Source dataset
uspto-grants-2012_07
Patent number
US08211885B2

Reaction notes

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