Triphenylphosphine → Triphenylphosphine

HRID 911263Notes

Reaction equation

HRID 911263 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)#[N:21].N(C(OCC)=O)=NC(O[CH2:34][CH3:35])=O>C1COCC1.CCOC(C)=O>[C:14]1([CH:34]([O:28][C:25]2[CH:26]=[CH:27][C:22]([C:20]#[N:21])=[CH:23][CH:24]=2)[CH3:35])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[C:14]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 130194-CyanophenolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 2

HCID 11776TriphenylphosphineYield 94.9%HCID 21711561HCID 21711561, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add triphenylphosphine (7.869 g, 30 mmol) to a solution of sec-phenylethyl alcohol (1.467 g, 12 mmol), 4-cyanophenol (1.191 g, 10 mmol) and diethyl azodicarboxylate (4.528 g, 26 mmol) in anhydrous THF (50 mL) at 0° C. Stir the reaction at ambient temperature for 12 h. Dilute with EtOAc, wash with brine, dry over Na2SO4, filter and concentrate. Purify by chromatography on silica gel eluting with EtOAc/hexane (1:8) to give (±)-4-(1-phenylethoxy)-benzonitrile with a small amount of triphenylphosphine (2.49 g total).

Workup

  1. customthe reaction at ambient temperature for 12 h
  2. washwash with brine
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by chromatography on silica gel eluting with EtOAc/hexane (1:8)

Sources & evidence

ORD record
ord-fcc0f2a099eb467d8e4236f701676f1a
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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