Hydrochloric Acid → HCID 86755967, compound

HRID 369661Notes

Reaction equation

HRID 369661 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:26][CH2:27][CH:28]=[C:29]([Cl:31])[Cl:30])[CH:5]=[C:6]([Cl:25])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH:16](O)[C:17](Cl)([Cl:22])[C:18]([F:21])([F:20])[F:19].N1C=CC=CC=1.C(OC(=O)C)(=O)C.Cl>CN(C1C=CN=CC=1)C.[Zn].CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:26][CH2:27][CH:28]=[C:29]([Cl:31])[Cl:30])[CH:5]=[C:6]([Cl:25])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15]/[CH:16]=[C:17](\[Cl:22])/[C:18]([F:21])([F:20])[F:19]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 23282421HCID 23282421, compound

Product 1

HCID 86755967HCID 86755967, compoundYield 79.2%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.57 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(4,4-dichloro-5,5,5-trifluoro-3-hydroxypentyloxy)butyloxy)benzene, 0.16 g of pyridine, 0.12 g of acetic anhydride, 10 mg of N,N-dimethyl-4-aminopyridine and 20 ml of N,N-dimethylformamide was stirred at room temperature for 30 minutes, to which 0.078 g of zinc dust was added. The reaction mixture was further stirred at room temperature for 1 hour, poured into 20 ml of diluted hydrochloric acid and extracted twice with 50 ml of diethyl ether. The diethyl ether layers were combined, washed with water, dried over magnesium sulfate and then evaporated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.41 g of (Z)-3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(4-chloro-5,5,5-trifluoro-3-pentenyloxy)butyloxy)benzene [the integrated CF3 signal ratio of Z/E=93/7 as determined by 19F-NMR (CDCl3 /CFCl3)] (yield, 79%), nD30.0 1.5057.

Workup

  1. additionwas added
  2. extractionextracted twice with 50 ml of diethyl ether
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto give a crude product

Sources & evidence

ORD record
ord-22ddad4f00144b99b644eb8e29810999
Source dataset
uspto-grants-2000_10
Patent number
US06140274

Reaction notes

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