Triphenylphosphine → HCID 43437959, compound

HRID 363004

Reaction equation

HRID 363004 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:31][CH:32](O)[CH3:33]>O1CCCC1>[Cl:31][CH2:32][CH2:33][O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 795792-Methyl-3-nitrophenolHCID 126390351-Chloroethan-1-ol

Product 1

HCID 43437959HCID 43437959, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methyl-3-nitro-phenol (3.0 g, 19.6 mmol), triphenylphosphine (7.2 g, 27.4 mmol), and chloroethanol (1.89 g, 23.5 mmol) in anhydrous tetrahydrofuran (70 mL) was slowly added a solution of diethylazidodicarboxylate (4.78 g, 27.4 mmol). After 1 h the reaction was complete and the solvent was removed and the residue dissolved in 1:1 ethyl acetate-hexanes (150 mL). After 30 min the solid triphenylphosphine oxide was filtered and the solvent again removed. The crude product was purified by chromatography (20% ethyl acetate-hexanes) to afford 4.2 g (100%) of a light yellow solid: mp 58°-59° C.

Workup

  1. customthe solvent was removed
  2. dissolutionthe residue dissolved in 1:1 ethyl acetate-hexanes (150 mL)
  3. filtrationAfter 30 min the solid triphenylphosphine oxide was filtered
  4. customthe solvent again removed
  5. customThe crude product was purified by chromatography (20% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-09699a53c86042dea23d305bfe9af001
Source dataset
uspto-grants-1999_02
Patent number
US05872144

Linked notes

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