Triphenylphosphine → Triphenylphosphine Oxide

HRID 974029Notes

Reaction equation

HRID 974029 reaction equation
FC1C=C(C(C)C(=O)C[OH:11])C=CC=1C1C=CC=CC=1.[C:20]1([P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)(Cl)(Cl)Cl>[C:33]1([P:26](=[O:11])([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 15676007HCID 15676007, compound

Product 1

HCID 13097Triphenylphosphine Oxide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 3-(2-fluoro-4-biphenylyl)-2-oxo-1-butanol (2.00 g, 7.74 mmol) in carbon tetrachloride (5 ml) was added triphenylphosphine (2.15 g, 8.20 mmol) at room temperature. After the addition, the mixture was stirred over night at room temperature, then concentrated to give triphenylphosphine oxide as precipitates. After filtration of the precipitates, the filtrates were evaporated under reduced pressure to a residue, which was chromatographed to afford 1-chloro-3-(2-fluoro-4-biphenylyl)-2-butanone (1.01 g, 47% yield) as crystalline materials: mp 57°-59° C.; NMR(CDCl3)δ 1.48(d, 3H), 4.07(m, 3H), 6.93-7.63(m, 8H); IR(neat) 1740, 1620, 1480, 1420, 1270 cm-1.

Workup

  1. additionAfter the addition
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-29d860e3f30e4306a7c057bdcda34744
Source dataset
uspto-grants-1991_11
Patent number
US05066666

Reaction notes

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