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p-Toluenesulfonic acid → (E)-6-methoxy-5-morpholino-2-(4-(trifluoromethyl)benzylidene)-2,3-dihydro-1H-inden-1-one

HRID 62253
Notes
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Reaction equation

HRID 62253 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7]/[C:8](=[CH:25]\[C:24]3[CH:23]=[CH:22][C:21]([C:20]([F:19])([F:29])[F:30])=[CH:28][CH:27]=3)/[C:9]2=[O:12])=[CH:5][C:4]=1[N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 679964-(Trifluoromethyl)benzaldehydeHCID 1179401286-Methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

Product 1

HCID 117940206(E)-6-methoxy-5-morpholino-2-(4-(trifluoromethyl)benzylidene)-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
120 °C

Procedure

To a solution of 13 (100 mg, 04048 mmol) in toluene 10 mL was added 4-(trifluoromethyl)benzaldehyde 84 (70.4 mg, 0.404 mmol). PTSA (153.9 mg, 0.809 mmol) was added to the reaction mass, then stirred at 120° C. for 6 h. The reaction mass was diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude 85 which was purified through flash chromatography by using 100-200 mesh silica gel. The compound 85 was eluted at 28% ethyl acetate in hexane to afford yellow coloured solid compound (E)-6-methoxy-5-morpholino-2-(4-(trifluoromethyl)benzylidene)-2,3-dihydro-1H-inden-1-one 85.

Workup

  1. washwashed with water (3×25 mL)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. concentrationconcentrated
  4. customto get the crude 85 which
  5. customwas purified through flash chromatography
  6. washThe compound 85 was eluted at 28% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9d530a18371d4bc7ad2425b0bc08caa1
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09446047B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes