Water → HCID 57124282, compound

HRID 439854Notes

Reaction equation

HRID 439854 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:23])=[C:5]2[C:19](=[CH:20][C:21]=1[CH3:22])[C:8]1[NH:9][C:10]3[CH:11]=[CH:12][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:14][C:15]=3[C:7]=1[CH2:6]2.C([SiH](CC)CC)C.O.[OH-].[Na+]>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[C:4]([CH3:23])=[C:5]2[C:19](=[CH:20][C:21]=1[CH3:22])[C@H:8]1[NH:9][C:10]3[CH:11]=[CH:12][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:14][C:15]=3[C@H:7]1[CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 22408506HCID 22408506, compound

Product 1

HCID 57124282HCID 57124282, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5,10-Dihydro-2-methoxy-1,3-dimethyl-8-isopropylindeno[1,2-b]indole (1.68 g, 5.5 mmol) was dissolved in trifluoroacetic acid (10 cm3) and stirred vigorously. Triethylsilane (1 cm3, 1.1 eq) was added, and stirring continued for 4 hours. The reaction was poured into water, stirred for 15 minutes, and neutralised with 2M NaOH. All organic material was extracted into ethyl acetate, washed with water and dried (Na2SO4 ). After removal of solvent, the solid material was recrystallised from 60°-80° petroleum ether as white needles. Yield: 1.18 g, 70% .M.p. 106° C. 1H NMR (CDCl3) δ: 7.05 (1H, s), 6.97 (1H, s), 6.88 (1H, dd, J=8.6 Hz), 6.55 (1H, d, J=8.1 Hz), 5.19 (1H, d, J=8.4 Hz), 4.18 (1H, ddd), 3.8 (1 H, br), 3.64 (3H, s), 3.36 (1H, dd, J=16.5, 8.3 Hz), 3.07 (1H, d(br) J=16.5 Hz), 2.81 (1H, septet, J=7.0 Hz), 2.25 (3H, s), 2.15 (3H, s), 1.20 (6H, d, J=7.0 Hz).

Workup

  1. stirringstirring
  2. stirringstirred for 15 minutes
  3. extractionAll organic material was extracted into ethyl acetate
  4. washwashed with water
  5. dry with materialdried (Na2SO4 )
  6. customAfter removal of solvent
  7. customthe solid material was recrystallised from 60°-80° petroleum ether as white needles

Sources & evidence

ORD record
ord-1291ddda5b344c429689934d1d17f519
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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