Tributylphosphine → benzyl 3-cyano-3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoate

HRID 922255Notes

Reaction equation

HRID 922255 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.[C:21]([CH:23]([C:35]1[CH:40]=[CH:39][C:38](O)=[CH:37][CH:36]=1)[CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])#[N:22].C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:21]([CH:23]([C:35]1[CH:36]=[CH:37][C:38]([O:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5]/[C:4](=[N:3]\[O:2][CH3:1])/[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:8][CH:9]=2)=[CH:39][CH:40]=1)[CH2:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])#[N:22]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 66685080Benzyl 3-cyano-3-(4-hydroxyphenyl)propanoateHCID 866957602-(4-Hydroxymethyl-phenoxy)-1-phenyl-ethanone O-methyl-oxime

Product 1

HCID 89790490benzyl 3-cyano-3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoateYield 80.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 50 mL RB flask fitted with magnetic stirrer was charged Toluene (20 mL). To the stirred solvent was added 2-(4-Hydroxymethyl-phenoxy)-1-phenyl-ethanone O-methyl-oxime (0.039 g, 0.14 mmol) and benzyl 3-cyano-3-(4-hydroxyphenyl)propanoate (0.04 g, 0.14 mmol) at 0° C. for 5 min. Then added tributylphosphine (0.043 g, 0.2 mmol) stirred at 0° C. for 15 min, was added 1,1′aza(dicarbonyl)dipiperidine (0.054 g, 0.2 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 to and evaporated, purified by 100-200 silica column using pet-ether and ethylacetate. The product obtained as a colourless oily liquid (0.06 g, 79.00%)

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 to and
  6. customevaporated
  7. custompurified by 100-200 silica column

Sources & evidence

ORD record
ord-7f1e2ed957fc4f5681a8a9cfabe49e28
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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