Tributylphosphine → Tributylphosphanium chloride

HRID 1835960Notes

Reaction equation

HRID 1835960 reaction equation
C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.C1C=CC(C[Cl:26])=CC=1.[CH2:27]([P:31]([CH2:36][CH2:37][CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH3:30]>C(Cl)Cl>[Cl-:26].[CH2:36]([PH+:31]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:32][CH2:33][CH2:34][CH3:35])[CH2:37][CH2:38][CH3:39]

Participants

4

Reactant 2

HCID 13831TributylphosphineHCID 16211592Merrifield's peptide resin

Product 1

HCID 21584914Tributylphosphanium chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Merrifield's peptide resin (Aldrich, 1.1 meq/g of Cl), 50.1 g was stirred in 250 mL of CH2Cl2 with 132.3 g of tri-n-butylphosphine under argon for 1 week. The slurry was filtered and the beads washed with 1.5 L of CH2Cl2. The product was dried in the air and then under vacuum to produce 61.9 g of tributylphosphonium chloride substituted polymer.

Workup

  1. filtrationThe slurry was filtered
  2. washthe beads washed with 1.5 L of CH2Cl2
  3. customThe product was dried in the air

Sources & evidence

ORD record
ord-09ccfa9a4d8745e495680a7403060883
Source dataset
uspto-grants-2004_08
Patent number
US06774249B2

Reaction notes

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