Triphenylphosphine → HCID 23448408, compound

HRID 1838782Notes

Reaction equation

HRID 1838782 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1.[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.O1CCCC1>[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][O:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 130194-CyanophenolHCID 900121-Octanol, 8-chloro-HCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 23448408HCID 23448408, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (7.3 g; 42 mmol) and tetrahydrofuran (15 ml) was added dropwise at 0° C. to a solution of 4-hydroxybenzonitrile (4.2 g; 35 mmol), 8-chloro-1-octanol (6.9 g; 42 mmol), triphenylphosphine (11.0 g; 42 mmol) and tetrahydrofuran (70 ml) and stirred at room temperature overnight. The reaction mixture was added to water (200 ml) and extracted with ethyl acetate (3×100 ml), dried over magnesium sulphate and filtered. The solvent was then removed in vacuo. The residue was purified by column flash chromatography on silica gel using toluene/ethyl acetate (97:3) as eluent, to give 8.8 g (94%) of p-[(8-chlorooctyl)oxy]benzonitrile.

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. customThe solvent was then removed in vacuo
  5. customThe residue was purified by column flash chromatography on silica gel

Sources & evidence

ORD record
ord-71965819f0fa43da846f36059c518f7c
Source dataset
uspto-grants-2004_01
Patent number
US06676851B1

Reaction notes

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