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Tributylphosphine → 2-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]acetonitrile

HRID 922256
Notes
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Reaction equation

HRID 922256 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9][CH:8]=1.O[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]#[N:30])=[CH:24][CH:23]=1.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:1][O:2]/[N:3]=[C:4](/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)\[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][O:14][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][C:29]#[N:30])=[CH:24][CH:23]=2)=[CH:9][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 265484-Hydroxybenzyl cyanideHCID 866957602-(4-Hydroxymethyl-phenoxy)-1-phenyl-ethanone O-methyl-oxime

Product 1

HCID 885813362-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]acetonitrileYield 62.9%

Reagents, catalysts & solvents 1

HCID 1140Toluene
Solvent

Procedure

To a 50 mL RB flask fitted with magnetic stirrer was charged dry Toluene. To the stirred solvent was added 2-(4-Hydroxymethyl-phenoxy)-1-phenyl-ethanone O-methyl-oxime (0.20 g, 0.74 mmol) and (4-hydroxyphenyl)acetonitrile (0.098 g, 0.74 mmol) at 0° C. for 5 min. Then added tributylphosphine (0.0.24 g, 1.2 mmol) stirred at 0° C. for 15 min, was added 1,1′aza(dicarbonyl)dipiperidine (0.303 g, 1.2 mmol), this resulting mass stirred at RT for 16 h, The solvent removed, the residue was extracted with ethyl acetate. The organic layer washed with water and brine solution and dried by anhydrous sodium sulphate and evaporated, purified by 100-200 silica column using pet-ether and ethylacetate. The product obtained as a colourless oily liquid (0.18 g, 60.00%)

Workup

  1. customTo a 50 mL RB flask fitted with magnetic stirrer
  2. customThe solvent removed
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer washed with water and brine solution
  5. dry with materialdried by anhydrous sodium sulphate
  6. customevaporated
  7. custompurified by 100-200 silica column

Sources & evidence

ORD record
ord-561d14d2a1594c90b5077b7fb9c65d25
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278915B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes