Triphenylphosphine → HCID 18504646, compound

HRID 1387231Notes

Reaction equation

HRID 1387231 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][CH:11]([CH2:13][CH2:14][OH:15])[CH2:10][O:9]2)=[CH:4][CH:3]=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.[Cl:49][C:50]([Cl:63])=[CH:51][CH2:52][O:53][C:54]1[CH:59]=[C:58]([Cl:60])[C:57](O)=[C:56]([Cl:62])[CH:55]=1>O1CCCC1>[Cl:60][C:58]1[CH:59]=[C:54]([O:53][CH2:52][CH:51]=[C:50]([Cl:63])[Cl:49])[CH:55]=[C:56]([Cl:62])[C:57]=1[O:15][CH2:14][CH2:13][CH:11]1[CH2:10][O:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[O:12]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenolHCID 18504564HCID 18504564, compound

Product 1

HCID 18504646HCID 18504646, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 0.4 g of 2-[2-(4-chlorophenyl)-1,3-dioxolan-4-yl]ethanol, 0.46 g of triphenylphosphine and 6 ml of tetrahydrofuran was added dropwise 0.35 ml of diisopropyl azodicarboxylate, while stirring at room temperature. After further stirring for 15 minutes, a solution of 0.5 g of 4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol in 2 ml of tetrahydrofuran was added. After stirring continued at room temperature for 3 hours, the reaction mixture was concentrated, and the residue was subjected to silica gel chromatography, which afforded 0.3 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[2-[2-(4-chlorophenyl)-1,3-dioxolan-4-yl]ethoxy]benzene (35% yield), m.p. 84.1° C.

Workup

  1. stirringAfter further stirring for 15 minutes
  2. stirringAfter stirring
  3. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-8e33cad7877d4f5bb434887a2ae859de
Source dataset
uspto-grants-2001_07
Patent number
US06268313B1

Reaction notes

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