Triethylsilane → HCID 53246024, compound

HRID 1189560Notes

Reaction equation

HRID 1189560 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:3]=1.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C([SiH](CC)CC)C.[C:44]1([S:50]([C:53]2[CH:60]=[CH:59][CH:58]=[CH:57][C:54]=2[CH:55]=O)(=[O:52])=[O:51])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C(Cl)Cl>[CH3:1][C:2]1[N:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[C:4]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:3]=1[CH2:55][C:54]1[CH:57]=[CH:58][CH:59]=[CH:60][C:53]=1[S:50]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)(=[O:52])=[O:51]

Participants

6

Reactant 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 6409162-(phenylsulfonyl)benzaldehydeHCID 58310920ethyl 2-(5-methyl-2,3-diphenyl-1H-pyrrol-1-yl)acetate

Product 1

HCID 53246024HCID 53246024, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

In a scintillation vial, ethyl 2-(5-methyl-2,3-diphenyl-1H-pyrrol-1-yl)acetate (0.3 g, 0.939 mmol) was dissolved in 10 mL of DCM and the mixture cooled to −78° C. Trimethylsilyl trifluoromethanesulfonate (0.382 ml, 2.113 mmol) was then added followed by triethylsilane (0.450 ml, 2.82 mmol). The resulting mixture was stirred at −78° C. for 30 minutes. At this time, 2-(phenylsulfonyl)benzaldehyde (0.231 g, 0.939 mmol) was added portionwise as a solution in 2.0 mL of DCM and the reaction evolution was monitored by LC/MS. Following addition of the aldehyde, the cold bath was removed and the reaction was stirred overnight (gradually warming to room temp). The reaction was quenched with a sodium bircarbonate solution and moved to a separatory funnel. Layers were separated and the aqueous portion was extracted 2 additional times with DCM. The organics were combined, dried, filtered, and concentrated. The crude oil was purified by column chromatography (SiO2) using a 0-40% EtOAc/hexane gradient to give ethyl 2-(2-methyl-4,5-diphenyl-3-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (294 mg, 0.535 mmol, 56.9% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 8.31-8.29 (m, 1H), 7.84-7.82 (m, 2H), 7.52-7.48 (m, 2H), 7.42-7.38 (m, 3H), 7.28-7.21 (m, 4H), 7.15-7.13 (m, 2H), 6.93-6.86 (m, 3H), 6.75-6.73 (m, 2H), 4.51 (s, 2H), 4.21 (q, 2H), 4.04 (s, 2H), 1.79 (s, 3H), 1.25 (t, 3H).

Workup

  1. customthe cold bath was removed
  2. stirringthe reaction was stirred overnight (
  3. temperaturegradually warming to room temp)
  4. customThe reaction was quenched with a sodium bircarbonate solution
  5. custommoved to a separatory funnel
  6. customLayers were separated
  7. extractionthe aqueous portion was extracted 2 additional times with DCM
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude oil was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-497b227ce2b34701b26c915e2b8dcbab
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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