Triethylsilane → HCID 20097788, compound

HRID 1769842Notes

Reaction equation

HRID 1769842 reaction equation
[N+:1]([C:4]1[CH:44]=[CH:43][C:7]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:26]4[CH:31]=[CH:30][C:29]([C:32](=O)[C:33]5[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=5)=[CH:28][CH:27]=4)[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([SiH](CC)CC)C>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:26]4[CH:31]=[CH:30][C:29]([CH2:32][C:33]5[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=5)=[CH:28][CH:27]=4)[CH2:21][CH2:20][CH:19]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)=[CH:43][CH:44]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 22919273HCID 22919273, compound

Product 1

HCID 20097788HCID 20097788, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

1,1-Bis[4-(4-nitrobenzoyl)phenyl]-4-butylcyclohexane 45.40 g was dissolved in dichloromethane 660 ml, and a solution of trifluorosulfuric acid 36.9 g in dichloromethane 860 ml was added dropwise for one hour. Then, a solution of triethylsilane 47.38 g in dichloromethane 80 ml was added dropwise for 90 minutes. When 30 minutes passed after the addition was finished, the ice bath was removed and the solution was stirred for five hours at room temperature. The finish of the reaction was confirmed by liquid chromatography, and then the reaction solution was neutralized with an aqueous solution of sodium carbonate and washed with water. After dichloromethane was removed with a rotary evaporator, the residue was dissolved in toluene, the solution was treated with an alumina column, and the solvent was distilled away from the elute to obtain 1,1-bis[4-(4-nitrobenzyl)phenyl]-4-butylcyclohexane 38.0 g.

Workup

  1. customWhen 30 minutes
  2. additionafter the addition
  3. customthe ice bath was removed
  4. washwashed with water
  5. customAfter dichloromethane was removed with a rotary evaporator
  6. dissolutionthe residue was dissolved in toluene
  7. additionthe solution was treated with an alumina column
  8. distillationthe solvent was distilled away from the
  9. washelute

Sources & evidence

ORD record
ord-4c7d2a189de34ab389b6ea6bedef31d0
Source dataset
uspto-grants-1995_01
Patent number
US05382688

Reaction notes

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