Water → HCID 15082728, compound

HRID 439861Notes

Reaction equation

HRID 439861 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:11]2[NH:10][C:9]3[C:14]4[C:19]([CH2:20][C:8]=3[C:7]=2[CH:6]=1)=[CH:18][CH:17]=[CH:16][CH:15]=4)([CH3:4])([CH3:3])[CH3:2].C([SiH](CC)CC)C.O.[OH-].[Na+]>FC(F)(F)C(O)=O>[C:1]([C:5]1[CH:13]=[CH:12][C:11]2[NH:10][C@@H:9]3[C:14]4[C:19]([CH2:20][C@@H:8]3[C:7]=2[CH:6]=1)=[CH:18][CH:17]=[CH:16][CH:15]=4)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 1229699HCID 1229699, compound

Product 1

HCID 15082728HCID 15082728, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5,10-dihydro-8-tert-butylindeno[1,2-b]indole (0.57 g, 2.2 mM) in trifluoroacetic acid (5 cm3) was stirred rapidly, and triethylsilane (0.7 cm3, 2 eq ) added in one portion. The reaction was stirred overnight, poured into water (10 cm3) and neutralised by the addition of sodium hydroxide. The product was extracted into diethyl ether (2×5 cm3), and the combined extracts were washed with water, dried (Na2SO4) and evaporated to yield a pink solid. This was washed with cold petroleum ether (60°-80° C.), and then crystallised from petrol to yield a colourless solid. Yield: 0.47 g, 81% M.p. 103°-105° C.; 1H NMR (CDCl3) δ: 7.4-6.9 (6H, m), 6.58 (1H, d, J=8 Hz), 5.25 (1H, d, J=8.5 Hz), 4.15 (2H, br.m), 3.5 (1H, dd, J=16.0 and 9 Hz), 3.2 (1H, d, J=16 Hz), 1.2 (9H, s).

Workup

  1. extractionThe product was extracted into diethyl ether (2×5 cm3)
  2. washthe combined extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto yield a pink solid
  6. washThis was washed with cold petroleum ether (60°-80° C.)
  7. customcrystallised from petrol
  8. customto yield a colourless solid

Sources & evidence

ORD record
ord-be9fae1dae094a1b954598d2a1489a1c
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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