Hydrochloric Acid → HCID 68229261, compound

HRID 2281030Notes

Reaction equation

HRID 2281030 reaction equation
[CH3:1][C:2]1[O:3][C:4](=[O:19])/[C:5](=[CH:7]\[C:8]2[O:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][CH:12]=2)/N=1.Cl.C([OH:23])C>>[OH:23]/[C:5](=[CH:7]\[C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:12]=1)/[C:4]([O:3][CH2:2][CH3:1])=[O:19]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 67450566HCID 67450566, compound

Product 1

HCID 68229261HCID 68229261, compoundYield 55%

Procedure

To an ethanol (10 mL) suspension of (E)-2-methyl-4-((5-phenylfuran-2-yl)methylene)oxazol-5(4H)-one 47 (253 mg, 1.0 mmol) was added 12M HCl (5 mL). The reaction mixture was refluxed for 5 h, then the excess solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), then washed with water (2×30 mL). The organic layer was dried with brine and MgSO4, then concentrated in vacuo. Flash column chromatography on silica gel (n-hexanes:ethyl acetate=10:1) of the residue afforded the desired product 48 in 55% yield (142 mg, yellow solid). 1H NMR (400 MHz, CDCl3): 7.70 (d, J=7.2 Hz, 2H), 7.39 (t, J=7.2 Hz, 2H), 7.27 (t, J=7.2 Hz, 1H), 6.97 (d, J=3.6 Hz, 1H), 6.78 (d, J=3.6 Hz, 1H), 6.65 (d, J=1.6 Hz, 1H), 6.43 (d, J=1.6 Hz, 1H), 4.37 (q, J=7.2 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. customthe excess solvent was removed in vacuo
  3. additionThe residue was diluted with ethyl acetate (100 mL)
  4. washwashed with water (2×30 mL)
  5. dry with materialThe organic layer was dried with brine and MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-805df31a7d6740578a67ce76d2d254c4
Source dataset
uspto-grants-2015_09
Patent number
US09139575B2

Reaction notes

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