Hydrochloric Acid → HCID 66616139, compound

HRID 2172142Notes

Reaction equation

HRID 2172142 reaction equation
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[Na+].C(C1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)=C.S([CH2:29][N+:30]#[C-])(C1C=CC(C)=CC=1)(=O)=O.Cl>CS(C)=O.O>[NH:30]1[CH:29]=[CH:3][C:2]([C:5]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=2)=[CH:1]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 161915Tosylmethyl isocyanideHCID 583124Methyl 4-ethenylbenzoateHCID 23676156Sodium t-butoxide

Product 1

HCID 66616139HCID 66616139, compoundYield 25.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

Sodium tert-butoxide (3.681 g, 38.3 mmol, 2.0 eq.) is suspended in anhydrous DMSO under nitrogen. To this a solution of methyl 4-vinylbenzoate (3.11 g 19.15 mmol, 1.0 eq.) and tosylmethyl isocyanide (4.86 g, 24.89 mmol, 1.3 eq.) in anhydrous DMSO is transferred via cannula. The dark brown mixture is stirred at room temperature for 16 hrs. The mixture is adjusted to pH 6 by addition of 10% HCl solution, diluted with water and extracted with ethyl acetate (3×50 mL). The combined organic extract is washed with water (2×50 mL) and brine, dried over sodium sulfate and concentrated. The crude residue is purified by silica gel chromatography (20-40% ethyl acetate/hexanes) to give 990 mg (4.92 mmol, 25.7%) of methyl 4-(1H-pyrrol-3-yl)-benzoate as a cream colored solid. MS (ES+): m/e 201.08. 1H NMR (300 MHz, CDCl3): δ 8.39 (1H, br s), 8.00 (2H, d, J−9 Hz), 7.58 (2H, d, J=9 Hz), 7.20 (1H, m), 6.85 (1H, m), 6.60 (1H, m), 3.91 (3H, s).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. extractionThe combined organic extract
  3. washis washed with water (2×50 mL) and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude residue is purified by silica gel chromatography (20-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7eff501b8d7e4172a5ef966f0ad72745
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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