Hydrochloric Acid → HCID 15230613, compound

HRID 1464810Notes

Reaction equation

HRID 1464810 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][C:14]1[O:15][C:16]2[CH:22]=[CH:21][C:20](/[CH:23]=[C:24](/[O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)\[C:25]#[N:26])=[CH:19][C:17]=2[CH:18]=1.O.C(OCC)(=[O:37])C.Cl>C(O)C.[OH-].[Na+]>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][C:14]1[O:15][C:16]2[CH:22]=[CH:21][C:20](/[CH:23]=[C:24](/[O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)\[C:25]([NH2:26])=[O:37])=[CH:19][C:17]=2[CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 15284466HCID 15284466, compound

Product 1

HCID 15230613HCID 15230613, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of (E)-3-[2-(5-methyl-2-phenyl-4-oxazolyl)methyl-5-benzofuranyl]-2-phenoxy-2-propenenitrile (0.19 g, 0.44 mmol) in ethanol (10 ml) and sodium hydroxide (2 ml) was heated to reflux for 24 hours, then cooled, poured into a mixture of water (50 ml) and ethyl acetate and acidified with 6N hydrochloric acid. The layers were separated, the aqueous layer was extracted with ethyl acetate and the combined organic phases were washed with brine, dried over magnesium sulfate and concentrated. The product was purified by flash chromatography (hexanes/ethyl acetate/acetic acid, 48:8:1) followed by recrystallization from ethyl acetate/hexanes (30 mg, m.p. 171°-172.5° C.).

Workup

  1. temperatureto reflux for 24 hours
  2. temperaturecooled
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic phases were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe product was purified by flash chromatography (hexanes/ethyl acetate/acetic acid, 48:8:1)
  9. customfollowed by recrystallization from ethyl acetate/hexanes (30 mg, m.p. 171°-172.5° C.)

Sources & evidence

ORD record
ord-3b98d25705a74e849c66a2d8bfdd4ef5
Source dataset
uspto-grants-1994_04
Patent number
US05306726

Reaction notes

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