Triphenylphosphine → HCID 19966088, compound

HRID 977879Notes

Reaction equation

HRID 977879 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][Br:12])=[CH:7][C:6]=1[NH:13][C:14](=[O:30])[CH2:15][CH:16]1[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:23][C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)([CH3:4])([CH3:3])[CH3:2].[C:31]1([P:37]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1(C)C=CC=CC=1>[Br-:12].[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][P+:37]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:7][C:6]=1[NH:13][C:14](=[O:30])[CH2:15][CH:16]1[C:29]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:23][C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 19966210HCID 19966210, compound

Product 1

HCID 19966088HCID 19966088, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.52 g (5.42 mmol) of N-[2-t-butyl-5-bromomethylphenyl]-2-(9H-xanthen-9-yl)acetamide [prepared as described in step (i) above] and 1.58 g (6.02 mmol) of triphenylphosphine in 25 ml of toluene was heated under reflux for 5 hours whilst vigorously stirring. At the end of this time, it was cooled to room temperature, and the resulting precipitate was collected by filtration and pulverized. This precipitate was then washed with toluene and with hexane, in that order, and dried over anhydrous sodium sulfate, to give 3.71 g (yield 90%) of the title compound as a powder.

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationthe resulting precipitate was collected by filtration
  3. washThis precipitate was then washed with toluene and with hexane, in that order
  4. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-7f4684ccf1144fb6b9734922265d97df
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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