Methanol → HCID 20066028, compound

HRID 2265115Notes

Reaction equation

HRID 2265115 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[C:10](/[CH3:17])=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].O1CCCC1.CO>[Fe].O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7](/[C:10](/[CH3:17])=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 614540480854-57-5

Product 1

HCID 20066028HCID 20066028, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Compound 19a (929 mg), iron powder (1.97 g), and ammonium chloride (436 mg) were added to a mixed solution of tetrahydrofuran (4 ml), methanol (4 ml), and water (4 ml). The obtained mixture was stirred at 70° C. for 3.5 hours. The mixture was allowed to cool and then filtered. The filtrate was separated with ethyl acetate and water. The organic layer was sequentially washed twice with water and once with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (17%-33% ethyl acetate/n-hexane) to obtain Compound 19b (757 mg, 96%) as an orange solid. 1H-NMR (CDCl3) δ7.35 (2H, d, J=8.7 Hz), 6.65 (2H, d, J=8.7 Hz), 6.09 (1H, s), 4.19 (2H, q, J=7.1 Hz), 3.85 (2H, brs), 2.54 (3H, s), 1.30 (3H, t, J=7.1 Hz).

Workup

  1. temperatureto cool
  2. filtrationfiltered
  3. customThe filtrate was separated with ethyl acetate and water
  4. washThe organic layer was sequentially washed twice with water and once with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by column chromatography (17%-33% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-bf93564a0c864673968bc48772fe99fa
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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