Benzoic Acid → HCID 68883930, compound

HRID 1294229Notes

Reaction equation

HRID 1294229 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][O:14][C:15]1[CH:16]=[C:17]([CH:28]=[CH:29][CH:30]=1)[CH2:18][S:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O.[C:31]([O:39][CH2:40][CH3:41])(=[O:38])[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[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][O:14][C:15]1[CH:16]=[C:17]([CH:28]=[CH:29][CH:30]=1)[CH2:18][S:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][CH:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:31]([O:39][CH2:40][CH3:41])=[O:38]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 7761Diethyl MalonateHCID 8082PiperidineHCID 86591572HCID 86591572, compound

Product 1

HCID 68883930HCID 68883930, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]benzaldehyde (0.80 g), diethyl malonate (0.37 g), benzoic acid (0.07 g), piperidine (0.05 g) and toluene (40 mL) was heated under reflux for 4 hrs. with azeotropic dehydration. The reaction mixture was concentrated, water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, dilute hydrochloric acid and water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give an oil from a fraction eluted with acetone-hexane (1:5, v/v). To a mixture of the obtained oil, tetrahydrofuran (20 mL) and ethanol (20 mL) was added sodium borohydride (0.02 g) at 0° C. and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was poured into water, acidified with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give diethyl 2-[3-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzylthio]benzyl]malonate as an oil (0.71 g, yield 66%) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hrs
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, dilute hydrochloric acid and water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customto give an oil from a fraction
  10. washeluted with acetone-hexane (1:5
  11. additionTo a mixture of the obtained oil, tetrahydrofuran (20 mL) and ethanol (20 mL)
  12. additionwas added sodium borohydride (0.02 g) at 0° C.
  13. additionThe reaction mixture was poured into water
  14. extractionextracted with ethyl acetate
  15. washThe organic layer was washed with water
  16. dry with materialdried over anhydrous magnesium sulfate
  17. concentrationconcentrated

Sources & evidence

ORD record
ord-88e503bb3fee455c8ab9135f13d6bc95
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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