Triphenylphosphine → 4-[2-(3-Iodophenoxy)ethyl]morpholine

HRID 1017561Notes

Reaction equation

HRID 1017561 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.O[CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[N:12]1([CH2:11][CH2:10][O:8][C:4]2[CH:3]=[C:2]([I:1])[CH:7]=[CH:6][CH:5]=2)[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 122723-IodophenolHCID 611632-MorpholinoethanolHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 184035554-[2-(3-Iodophenoxy)ethyl]morpholineYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-iodophenol (2.2 g, 10 mmol), N-(2-hydroxyethyl)morpholine (2 eq. 2.4 mL) and Ph3P (2 eq. 5.24 g) in THF (90 mL)at 0° C. was added dropwise a solution of diisopropylazodicarboxylate (2 eq. 3.96 g) in THF (20 mL). The resulting solution was stirred at room temperature overnight and was then quenched with NaHCO3. The product was extracted with EtOAc and the EtOAc layer was washed with NaCl (sat.), dried over sodium sulfate. The crude mixture was then purified on a silica gel column with 25% acetone in hexane to give 3-(2-morpholin-4-ylethyloxy)iodobenzene (2.8 g, 84% yield).

Workup

  1. customwas then quenched with NaHCO3
  2. extractionThe product was extracted with EtOAc
  3. washthe EtOAc layer was washed with NaCl (sat.)
  4. dry with materialdried over sodium sulfate
  5. customThe crude mixture was then purified on a silica gel column with 25% acetone in hexane

Sources & evidence

ORD record
ord-6b3911bc5994468f921f19f3847911a8
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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