Triphenylphosphine → 1-Benzyloxy-3,5-dichloro-4-(3-(4-trifluoromethylbenzamido)propyloxy)benzene

HRID 377725

Reaction equation

HRID 377725 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6]([C:7]([NH:9][CH2:10][CH2:11][CH2:12][OH:13])=[O:8])=[CH:5][CH:4]=1.[CH2:18]([O:25][C:26]1[CH:31]=[C:30]([Cl:32])[C:29](O)=[C:28]([Cl:34])[CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([Cl:34])[C:29]([O:13][CH2:12][CH2:11][CH2:10][NH:9][C:7](=[O:8])[C:6]2[CH:14]=[CH:15][C:3]([C:2]([F:16])([F:17])[F:1])=[CH:4][CH:5]=2)=[C:30]([Cl:32])[CH:31]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 120841702,6-Dichloro-4-benzyloxyphenolHCID 220068303-(4-Trifluoromethylbenzamido)propan-1-ol

Product 1

HCID 220068441-Benzyloxy-3,5-dichloro-4-(3-(4-trifluoromethylbenzamido)propyloxy)benzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A reaction vessel was charged with 5.25 g (21.2 mmol) of 3-(4-(trifluoromethyl)benzamido)propan-1-ol, 5.72 g (21.2 mmol) of 4-benzyloxy-2,6-dichlorophenol, 5.29 g (20.2 mmol) of triphenylphosphine and 100 ml of tetrahydrofuran, and a solution of 4.08 g (20.2 mmol) of diisopropyl azodicarboxylate dissolved in 20 ml of tetrahydrofuran was added dropwise, while stirring. After stirring at room temperature for 12 hours, the reaction mixture was concentrated, and the residue was subjected to silica gel chromatography, which afforded 1-benzyloxy-3,5-dichloro-4-(3-(4-trifluoromethylbenzamido)propyloxy)benzene.

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring at room temperature for 12 hours
  3. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-4590a0bc75254f4da4339f7a5b706abb
Source dataset
uspto-grants-2000_02
Patent number
US06028100

Linked notes

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