Hexachloroethane → HCID 23589036, compound

HRID 489722Notes

Reaction equation

HRID 489722 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:25][N:26]([CH3:28])[CH3:27])=[CH:8][N:9]2[Si:12]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:17]([CH3:20])([CH3:19])[CH3:18])[C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:5][CH:4]=1.C([Li])(C)(C)C.[Cl:34]C(Cl)(Cl)C(Cl)(Cl)Cl>CCOCC>[Cl:34][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[C:10]2[C:6]=1[C:7]([CH2:25][N:26]([CH3:28])[CH3:27])=[CH:8][N:9]2[Si:12]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:13]([CH3:14])([CH3:15])[CH3:16])[C:17]([CH3:19])([CH3:18])[CH3:20]

Participants

5

Reactant 3

HCID 6214HexachloroethaneHCID 23589038HCID 23589038, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 23589036HCID 23589036, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (6-methoxy-1-tri-tert-butylsilanyl-1H-indol-3-ylmethyl)-dimethylamine (0.2 g, 0.56 mmol) in anhydrous ether (20 ml) at −78° C. was added tert-butyllithium (43 mg, 0.67 mmol, 1.7M in pentane) dropwise. After being stirred for 20 min, the mixture was allowed to warm to 0° C. and was stirred for one hour. The mixture was then re-cooled to −78° C., and a solution of hexachloroethane (0.2 g, 0.84 mmol) in anhydrous ether (10 ml) was added over 10 min. The reaction mixture was warmed to room temperature and stirring was continued for another 1.5 hour before quenching with saturated ammonium chloride solution. After extracting into ether, the ether extract was dried (anhydrous sodium sulfate), and concentrated under reduced pressure to give (4-Chloro-6-methoxy-1-tri-tert-butylsilanyl-1H-indol-3-ylmethyl)-dimethylamine as an oil (0.217 g, 98.6%). 1H NMR (CDCl3) δ:1.12 (d, 18H, J=7.52 Hz), 1.66 (m, 3H), 2.30 (s, 6H), 3.75 (s, 2H), 3.80 (s, 3H), 6.78 (d, 1H, J=2.2 Hz), 6.88 (d, 1H, J=2.2 Hz), 7.02 (s, 1H).

Workup

  1. stirringwas stirred for one hour
  2. temperatureThe mixture was then re-cooled to −78° C.
  3. temperatureThe reaction mixture was warmed to room temperature
  4. stirringstirring
  5. waitwas continued for another 1.5 hour
  6. custombefore quenching with saturated ammonium chloride solution
  7. extractionAfter extracting into ether
  8. extractionthe ether extract
  9. dry with materialwas dried (anhydrous sodium sulfate)
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bbb26093e881401fa29eee79fec5ead7
Source dataset
uspto-grants-2005_12
Patent number
US06979696B2

Reaction notes

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