Triphenylphosphine → HCID 23282356, compound

HRID 369654Notes

Reaction equation

HRID 369654 reaction equation
[Cl:1][C:2]([Cl:10])=[CH:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][OH:9].[Cl:11][C:12]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([Cl:24])[C:13]=1O.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>[Cl:11][C:12]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]=[C:21]([Cl:23])[Cl:22])[CH:15]=[C:14]([Cl:24])[C:13]=1[O:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][CH:3]=[C:2]([Cl:10])[Cl:1]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenolHCID 23282394HCID 23282394, compound

Product 1

HCID 23282356HCID 23282356, compoundYield 4.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1.30 g of 3-(3,3-dichloro-2-propenyloxy)propanol, 2.02 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 1.89 g of triphenylphosphine and 20 ml of tetrahydrofuran was slowly added dropwise 1.42 g of diisopropyl azodicarboxylate with stirring under ice cooling. After stirring at room temperature for 24 hours, the reaction mixture was concentrated. The residue was subjected to silica gel chromatography, which afforded 0.15 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(3-(3,3-dichloro-2-propenyloxy)propyloxy)benzene (yield, 4.7%), nD18.5 1.5530.

Workup

  1. stirringAfter stirring at room temperature for 24 hours
  2. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-70fc5be304b44bfca6356833d1bf1f22
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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