Sodium Hydroxide → 1-(4,5-diphenyloxazol-2-yl)methylamino-2,3-dihydro-4-methoxy-1H-indene

HRID 1741370Notes

Reaction equation

HRID 1741370 reaction equation
FC(F)(F)C([N:5]([CH:24]1[C:32]2[C:27](=[C:28]([O:33][CH3:34])[CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25]1)[CH2:6][C:7]1[O:8][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1)=O.[OH-].[Na+]>CO>[C:12]1([C:10]2[N:11]=[C:7]([CH2:6][NH:5][CH:24]3[C:32]4[C:27](=[C:28]([O:33][CH3:34])[CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25]3)[O:8][C:9]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 183673231-(N-trifluoroacetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene

Product 1

HCID 183673131-(4,5-diphenyloxazol-2-yl)methylamino-2,3-dihydro-4-methoxy-1H-indeneYield 81.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[N-trifluoroacetyl-N-[(4,5-diphenyloxazol-2-yl)methyl]amino]-2,3-dihydro-4-methoxy-1H-indene (0.29 g) of methanol (2 ml) was added 1N NaOH aqueous solution (2 ml). The mixture was refluxed for 1 day and the solvent was removed in vacuo. The residue was extracted with ethyl acetate, dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-(4,5-diphenyloxazol-2-yl)methylamino-2,3-dihydro-4-methoxy-1H-indene (0.19 g). MS (m/z): 397 (M+ +1) NMR (CDCl3, δ): 1.85-2.10 (1H, m), 2.10 (1H, br), 2.33-2.52 (1H, m), 2.68-2.87 (1H, m), 2.92-3.12 (1H, m), 3.82 (3H, s), 4.14 (2H, s), 4.45 (1H, t, J=6.1 Hz), 6.74 (1H, d, J=7.9 Hz), 7.05 (1H, d, J=7.4 Hz), 7.20 (1H, dd, J=7.4, 7.9 Hz), 7.32-7.40 (6H, m), 7.57-7.67 (4H, m)

Workup

  1. temperatureThe mixture was refluxed for 1 day
  2. customthe solvent was removed in vacuo
  3. extractionThe residue was extracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1f72bbdd5d6f45b08ad3da09414a7f41
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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