Triphenylphosphine → [2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzyl]triphenylphosphonium chloride

HRID 1766651Notes

Reaction equation

HRID 1766651 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][C:14]2[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[C:19]3[C:15]=2[CH2:16][CH2:17][CH2:18]3)=[CH:11][C:10]=1[CH2:29][Cl:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[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>[Cl-:30].[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][C:14]2[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[C:19]3[C:15]=2[CH2:16][CH2:17][CH2:18]3)=[CH:11][C:10]=1[CH2:29][P+:37]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 230311674-(4-Benzyloxy-3-chloromethylphenoxy)-5-methyl-7-nitroindane

Product 1

HCID 21110566[2-Benzyloxy-5-(5-methyl-7-nitroindan-4-yloxy)benzyl]triphenylphosphonium chlorideYield 75.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 4-(4-benzyloxy-3-chloromethylphenoxy)-5-methyl-7-nitroindane (2.04 g) and triphenylphosphine (1.39 g) in toluene (50 mL) was heated under reflux for 12 hours. The reaction mixture was allowed to cool to room temperature. Precipitate was collected by filtration, and washed with diethyl ether to give the title compound (2.50 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. filtrationPrecipitate was collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-1b7df68d66524eb98830733f71adbc8f
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

Loading…