Water → HCID 86628206, compound

HRID 1821362Notes

Reaction equation

HRID 1821362 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[N:2]1.CO[CH:21]1[CH2:25][CH:24]([CH:26]=O)[CH:23](OC)[O:22]1.O>C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[CH:21]=[CH:25][C:24]([CH:23]=[O:22])=[CH:26]2)=[N:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehydeHCID 69001756HCID 69001756, compound

Product 1

HCID 86628206HCID 86628206, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Compound 2 (0.30 g, 1.3 mmol) was dissolved in acetic acid (5.0 mL) and 2,5-dimethoxy-4-tetrahydrofurancarbaldehyde (0.36 mL, 2.6 mmol) was added, followed by heating under reflux for 3 days. The reaction mixture was added with water and filtered through Celite, extracted with ethyl acetate and the organic layer was concentrated. The mixture was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to ethyl acetate) to obtain Compound 167 (88 mg, 22%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 days
  3. filtrationfiltered through Celite
  4. extractionextracted with ethyl acetate
  5. concentrationthe organic layer was concentrated
  6. customThe mixture was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to ethyl acetate)

Sources & evidence

ORD record
ord-766f111485d6405b85f2493e1e3cba62
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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