Triphenylphosphine → HCID 21541001, compound

HRID 1075844Notes

Reaction equation

HRID 1075844 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10][Br:11])=[O:4].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(#N)C>[Br-:11].[CH3:1][C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]([CH2:7][CH2:8][CH2:9][CH2:10][P+:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])=[O:4]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 21540995HCID 21540995, compound

Product 1

HCID 21541001HCID 21541001, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.82 g. (6.80 mmoles) of the N-trimethylacetyl-5-bromovaleramide prepared above and 2.67 g. (10.2 mmoles) of triphenylphosphine in 18 ml. of acetonitrile was heated to reflux under nitrogen for 96 hours. The solution was concentrated and the resultant solid was triturated with benzene (4x). The triturated solid was purified by silica gel column chromatography using first ethyl acetate to remove high Rf impurities then with a 9:1 mixture of methylene chloride:methanol. The salt, [4-trimethylacetylaminocarbonylbutyl]triphenylphosphonium bromide, was obtained as crystals from methylene chloride:ethyl acetate weighing 0.750 g. melting at 133.5°-138°.

Workup

  1. temperatureto reflux under nitrogen for 96 hours
  2. concentrationThe solution was concentrated
  3. customthe resultant solid was triturated with benzene (4x)
  4. customThe triturated solid was purified by silica gel column chromatography
  5. customto remove high Rf impurities
  6. additionwith a 9:1 mixture of methylene chloride

Sources & evidence

ORD record
ord-64c9def88db5419ea21dc114c5ab8788
Source dataset
uspto-grants-1976_05
Patent number
US03954741

Reaction notes

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