Triethylamine → HCID 23567805, compound

HRID 1797421Notes

Reaction equation

HRID 1797421 reaction equation
C(=O)(O[CH:5]1[CH:9]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:7]=[CH:6]1)OC.[C:28]1([S:34]([CH2:37][N+:38]([O-:40])=[O:39])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:38]([CH:37]([CH:5]1[CH:9]([CH2:10][O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:8]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:7]=[CH:6]1)[S:34]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)(=[O:36])=[O:35])([O-:40])=[O:39]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 88854((Nitromethyl)sulphonyl)benzeneHCID 86594453HCID 86594453, compound

Product 1

HCID 23567805HCID 23567805, compoundYield 108.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a round bottomed flask equipped with an argon inlet, a magnetic stirrer and a cooling bath was dissolved crude 10 (9.8 g, 26.5 mmol), phenylsulfonylnitromethane (5.4 g, 26.8 mmol) and tetrakis(triphenylphosphine)palladium (0.6 g, 0.52 mmol) in THF (80 mL) at 0° C. The reaction mixture was degassed using argon for a few minutes. Triethylamine (8.4 g, 11.1 mL, 79.5 mmol) was added to the reaction mixture over the course of 10 minutes at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and allowed to warm to room temperature. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was then quenched with 2 N HCl at 0° C. (100 mL) and extracted with hexane/ethyl acetate (1:1; 2×30 mL). The combined organic layer was washed with brine (100 mL), dried (sodium sulfate), and concentrated in vacuo to afford a red-colored oily residue. Silica pad filtration was conducted using ethyl acetate to remove the baseline materials and give the title compound (14.2 g crude, >100%) as a light brown oil which was used in the next step without any further purification.

Workup

  1. customTo a round bottomed flask equipped with an argon inlet, a magnetic stirrer and a cooling bath
  2. customThe reaction mixture was degassed
  3. customfor a few minutes
  4. temperatureto warm to room temperature
  5. stirringThe reaction mixture was stirred at room temperature for 3 hours
  6. customThe reaction mixture was then quenched with 2 N HCl at 0° C. (100 mL)
  7. extractionextracted with hexane/ethyl acetate (1:1; 2×30 mL)
  8. washThe combined organic layer was washed with brine (100 mL)
  9. dry with materialdried (sodium sulfate)
  10. concentrationconcentrated in vacuo
  11. customto afford a red-colored oily residue
  12. filtrationSilica pad filtration
  13. customto remove the baseline materials

Sources & evidence

ORD record
ord-a3b641621e204c139bc18450593a5a1d
Source dataset
uspto-grants-2006_04
Patent number
US07034152B2

Reaction notes

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