Sulfuryl chloride → Ethyl 2-chloro-4H-furo[3,2-b]pyrrole-5-carboxylate

HRID 1363295Notes

Reaction equation

HRID 1363295 reaction equation
S(Cl)([Cl:4])(=O)=O.[O:6]1[C:13]2[CH:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:10][C:9]=2[CH:8]=[CH:7]1>CCOCC>[Cl:4][C:7]1[O:6][C:13]2[CH:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[NH:10][C:9]=2[CH:8]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 12733395Ethyl 4H-furo[3,2-b]pyrrole-5-carboxylate

Product 1

HCID 44118832Ethyl 2-chloro-4H-furo[3,2-b]pyrrole-5-carboxylateYield 44.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a N2 atmosphere, sulfuryl chloride (0.15 mL, 1.85 mmol) was added dropwise over 10 min to a stirring solution of ethyl 4H-furo[3,2-b]pyrrole-5-carboxylate (300 mg, 1.67 mmol) in ether (7.5 mL). The reaction was stirred at rt for 4 h. The solvent was removed in vacuo. The residue was taken up in DCM and washed with H2O (1×) and brine (1×), then dried with Na2SO4, filtered and concentrated. Purification by HPLC gave 160 mg of ethyl 2-chloro-4H-furo[3,2-b]pyrrole-5-carboxylate. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.98 (s, 1H), 6.76 (s, 1H), 6.34 (s, 1H), 4.35 (q, 2H), 1.38 (t, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with H2O (1×) and brine (1×)
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by HPLC

Sources & evidence

ORD record
ord-9724031cadfe4911967c91ab9be5d38f
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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