Triphenylphosphine → HCID 15859799, compound

HRID 363057Notes

Reaction equation

HRID 363057 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]([OH:13])=[C:8]([Cl:14])[CH:7]=1.[C:16]1([CH2:22][CH2:23][CH2:24][CH2:25]O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[Cl:14][C:8]1[CH:7]=[C:6]([O:5][CH2:4][CH:3]=[C:2]([Cl:1])[Cl:15])[CH:11]=[C:10]([Cl:12])[C:9]=1[O:13][CH2:25][CH2:24][CH2:23][CH2:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 76889BenzenebutanolHCID 5462977Diethyl azodicarboxylateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Product 1

HCID 15859799HCID 15859799, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.30 g of 4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol, 0.16 g of 4-phenyl-1-butanol and 0.27 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.21 g of diethylazodicarboxylate dissolved in 5 ml of tetrahydrofuran was added dropwise, while stirring at room temperature. After stirring at room temperature for 24 hours, the reaction mixture was concentrated to obtain a residue. The residue was subjected to silica gel chromatography, which afforded 0.32 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-phenylbutyloxy)benzene (73% yield), nD26.0 1.5716.

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring at room temperature for 24 hours
  3. concentrationthe reaction mixture was concentrated
  4. customto obtain a residue

Sources & evidence

ORD record
ord-eb6a80056836446e8022851ccd38422d
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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