Triphenylphosphine → HCID 23282352, compound

HRID 369664Notes

Reaction equation

HRID 369664 reaction equation
[Cl:1][C:2]#[C:3][CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].[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:10][CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][C:3]#[C:2][Cl:1]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenolHCID 23282419HCID 23282419, compound

Product 1

HCID 23282352HCID 23282352, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 0.20 g of 4-(3-chloro-2-propynyloxy)butanol, 0.32 g of 2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenol, 0.32 g of triphenylphosphine and 15 ml of tetrahydrofuran was slowly added dropwise 0.27 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 0.38 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3-chloro-2-propynyloxy)butyloxy)benzene (yield, 71%), nD23.5 1.5511.

Workup

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

Sources & evidence

ORD record
ord-dcf998ab5c0142d1bcbb9cfc7e2b4146
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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