Iodine → HCID 131734388, compound

HRID 1508539Notes

Reaction equation

HRID 1508539 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10]2)=[CH:5][CH:4]=1.[I:18]I>CO.S([O-])([O-])(=O)=O.[Ag+2]>[I:18][C:8]1[CH:7]=[C:6]([C@H:9]2[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10]2)[CH:5]=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 807IodineHCID 86704607HCID 86704607, compound

Product 1

HCID 131734388HCID 131734388, compound

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl trans-3-(4-methoxyphenyl)cyclopentanecarboxylate (Step B) 60 mg, 0.256 mmol) in MeOH (2 ml), under nitrogen at RT, was added silver sulfate (80 mg, 0.256 mmol) followed by iodine (65.0 mg, 0.256 mmol). The resulting mixture was stirred at room temperature for 1 hour, then, filtered solids washing with MeOH and concentrated filtrate. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc in hexanes to afford the titled compound. 1H NMR (500 MHz, CDCl3): δ 7.63 (d, J=2.2 Hz, 1H); 7.15 (dd, J=8.4, 2.2 Hz, 1H); 6.75 (d, J=8.4 Hz, 1H); 3.85 (s, 3H); 3.70 (s, 3H); 3.12 (m, 1H); 3.00 (m, 1H); 2.33 (ddd, J=13.2, 8.0, 4.6 Hz, 1H); 2.17-2.10 (m, 2H); 1.94 (m, 1H); 1.83 (m, 1H); 1.61 (m, 1H).

Workup

  1. filtrationfiltered solids
  2. washwashing with MeOH and concentrated filtrate
  3. customThe residue was purified by flash column chromatography on silica gel
  4. washeluting with EtOAc in hexanes

Sources & evidence

ORD record
ord-0da38d9f7a40423ca9f34efe66d73a97
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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