Ethanol → Ethyl diphenylphosphinite

HRID 482637Notes

Reaction equation

HRID 482637 reaction equation
[C:1]1([P:7](Cl)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([OH:17])[CH3:16].N1C=CC=CC=1>CCOCC>[C:1]1([P:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:17][CH2:15][CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1049PyridineHCID 66180Chlorodiphenylphosphine

Product 1

HCID 69754Ethyl diphenylphosphinite

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diphenylphosphinous chloride (135 mmol) in dry ether (120 mL) was treated dropwise at 5° C. with a solution of ethanol (200 mmol) and pyridine (134 mmol) in ether (120 mL). After addition was complete, the mixture was warmed to room temperature, filtered under argon, and the solid hydrochloride washed with ether. Evaporation of the solvent gave an oil which was purified by Kugelrohr distillation at 95° C. (0.1 mmHg). Yield: 119 mmol (88%); 1H NMR (CDCl3) δ7.6-7.2 (m, 10H), 3.95 (doublet of quartets, JH-H =7 Hz, JP-H =10 Hz, 2H), 1.30 (t, J=7 Hz, 3H).

Workup

  1. additionAfter addition
  2. filtrationfiltered under argon
  3. washthe solid hydrochloride washed with ether
  4. customEvaporation of the solvent
  5. customgave an oil which
  6. distillationwas purified by Kugelrohr distillation at 95° C. (0.1 mmHg)

Sources & evidence

ORD record
ord-d088836813ae4c048c9097d685fbed49
Source dataset
uspto-grants-1986_03
Patent number
US04574060

Reaction notes

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