Ethyl Acetate → 5-(Tert-butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)-pentanenitrile

HRID 406373

Reaction equation

HRID 406373 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1)[CH2:22][C:23]([NH2:25])=O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCN=C1CCCCC2.P(Cl)(Cl)(OC)=O.C(OCC)(=O)C>C(Cl)Cl.CCCCCCC>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:26]1[CH:27]=[CH:28][C:29]([C:32]([F:33])([F:34])[F:35])=[CH:30][CH:31]=1)[CH2:22][C:23]#[N:25])([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 69611Methyl dichlorophosphateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 666301385-(Tert-butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)pentanoic acid amide

Product 1

HCID 667780115-(Tert-butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)-pentanenitrileYield 97.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8900HeptaneSolvent

Procedure

5-(tert-Butyldiphenylsilanyloxy)-3-(4-trifluoromethylphenyl)pentanoic acid amide (640 mg) was dissolved in methylene chloride (13 mL), and 1,8-diazabicyclo[5,4,0]undec-7-ene (862 μL) and methyl dichlorophosphate (301 μL) were added at 0° C. After stirring at room temperature for 1.5 hours, the reaction was terminated with a saturated sodium bicarbonate aqueous solution. The organic layer was washed with brine and then dried over magnesium sulfate. Concentration under reduced pressure gave an oil. The oil was allowed to pass through a silica gel pad (mobile phase:ethyl acetate:heptane=1:2) to obtain the title compound (600 mg).

Workup

  1. customthe reaction was terminated with a saturated sodium bicarbonate aqueous solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentration under reduced pressure
  5. customgave an oil

Sources & evidence

ORD record
ord-0c8a6ef0d45e484282c68aa172cda9a4
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Linked notes

Loading…