Water → HCID 67324468, compound

HRID 518139Notes

Reaction equation

HRID 518139 reaction equation
I(Cl)(=O)=O.[I:5](Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.[CH2:20]1[CH2:24][N:23](C(OC(C)(C)C)=O)[CH:22]2[CH2:32][O:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:39]=3[CH:21]12.C(Cl)Cl.O>C(O)(=O)C.[Cl-].[Zn+2].[Cl-]>[I:5][C:37]1[CH:36]=[CH:35][C:34]2[O:33][CH2:32][CH:22]3[CH:21]([C:39]=2[CH:38]=1)[CH2:20][CH:24]=[N:23]3

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 56924451Trimethylbenzylammonium DichloroiodateHCID 69930617HCID 69930617, compound

Product 1

HCID 67324468HCID 67324468, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Zinc chloride (2.49 g, 18.3 mmol) and benzyltrimethylammonium dichloroiodate (4.25 g, 12.2 mmol) were added to a suspension of tert-butyl 1,3a,4,9b-tetrahydrochromeno[3,4-b]pyrrole-3(2H)-carboxylate (2.8 g, 10.2 mmol) in acetic acid (30 mL). The reaction mixture was stirred at 50° C. for 16 h, cooled to r.t. and DCM (60 mL) was added followed by H2O (60 mL). The layers were separated. The organic layer was washed with H2O (2×) and saturated NaHSO3 (15 mL), and the solvent was evaporated to afford 8-iodo-1,3a,4,9b-tetrahydrochromeno[3,4-b]pyrrole, which was taken directly in the next step.

Workup

  1. temperaturecooled to r.t.
  2. customThe layers were separated
  3. washThe organic layer was washed with H2O (2×) and saturated NaHSO3 (15 mL)
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1c10ceaeee5348f68d6bde682f4a35f5
Source dataset
uspto-grants-2015_08
Patent number
US09115147B2

Reaction notes

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