Iodine → HCID 59444532, compound

HRID 1513997Notes

Reaction equation

HRID 1513997 reaction equation
II.[CH3:3][O:4][C:5]([CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:8]([O:10][CH3:11])=[O:9])=[O:6]>CO>[OH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:7]([C:5]([O:4][CH3:3])=[O:6])[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 807IodineHCID 68480331HCID 68480331, compound

Product 1

HCID 59444532HCID 59444532, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Iodine (1.0 g, 7.9 mmol) was dissolved in MeOH (100 mL). Compound 15 (4.5 g, 9.5 mmol) was added, and the mixture was stirred at 50° C. for one hour. The reaction mixture was evaporated to dryness. The residue was dissolved in CH2Cl2 and washed with 10% Na2SO3 (40 mL). The organic phase was dried with Na2SO4 and evaporated to dryness. Purification on silica gel (petroleum ether, by 40-60° C./ethyl acetate 10:1→5:3) yielded 1.96 g (89%) of the title compound.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with 10% Na2SO3 (40 mL)
  4. dry with materialThe organic phase was dried with Na2SO4
  5. customevaporated to dryness
  6. customPurification on silica gel (petroleum ether, by 40-60° C./ethyl acetate 10:1→5:3)

Sources & evidence

ORD record
ord-5d957e5ae2134850a97e2e87c92800b3
Source dataset
uspto-grants-2012_07
Patent number
US08221719B2

Reaction notes

Loading…