Triphenylphosphine → HCID 54089073, compound

HRID 363059Notes

Reaction equation

HRID 363059 reaction equation
[Cl:1][C:2]([Cl:15])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9](O)=[C:8]([Cl:14])[CH:7]=1.[O:16]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[Cl:14][C:8]1[CH:7]=[C:6]([O:5][CH2:4][CH:3]=[C:2]([Cl:15])[Cl:1])[CH:11]=[C:10]([Cl:12])[C:9]=1[CH2:26][C:25]1[CH:28]=[CH:29][CH:30]=[C:23]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:24]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 262953-Phenoxybenzyl alcoholHCID 5363146Diisopropyl azodicarboxylateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Product 1

HCID 54089073HCID 54089073, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.33 g of 4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol, 0.23 g of m-phenoxybenzyl alcohol and 0.34 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.26 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was concentrated, and then mixed with 20 ml of diethyl ether. The precipitate was filtered, and the filtrate was concentrated. The residue was subjected to silica gel chromatography, which afforded 0.31 g of 3,5-dichloro-4-(3-phenoxybenzyl)-1-(3,3-dichloro-2-propenyloxy)-benzene (57% yield), nD25.5 1.6066.

Workup

  1. stirringAfter stirring at room temperature for 12 hours
  2. concentrationthe reaction mixture was concentrated
  3. additionmixed with 20 ml of diethyl ether
  4. filtrationThe precipitate was filtered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0e287915e59447b6b54d09ad0796731e
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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