Dichloromethane → Trioctylphosphonium chloride

HRID 1265216Notes

Reaction equation

HRID 1265216 reaction equation
C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.C1C=CC(C[Cl:26])=CC=1.C(Cl)Cl.[CH2:30]([P:38]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>CN(C=O)C>[Cl-:26].[CH2:47]([PH+:38]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 20851TrioctylphosphineHCID 16211592Merrifield's peptide resin

Product 1

HCID 23501337Trioctylphosphonium chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Merrifield's peptide resin (Aldrich, 1.1 meq/g of Cl), 20.0 g was stirred in a solution of 100 mL of CH2Cl2 and 100 mL of dry DMF with 92.4 g of tri-n-octylphosphine under argon. The slurry was filtered and the beads washed with 3×200 mL of CH2Cl2. The product was dried in the air and then under vacuum to produce 21.2 g of trioctylphosphonium chloride substituted polymer.

Workup

  1. filtrationThe slurry was filtered
  2. washthe beads washed with 3×200 mL of CH2Cl2
  3. customThe product was dried in the air

Sources & evidence

ORD record
ord-45beed89f8344570bab07d8cbe2bb27c
Source dataset
uspto-grants-2003_04
Patent number
US06545102B1

Reaction notes

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