methyl 3-(3-hydroxyphenyl)propanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The operation is carried out as in Preparation 1 (Method 2) starting from 270 mg of the phenol prepared in Stage A, 309 mg of 1,1-dimethyl-ethyl N-[(phenylmethoxy)carbonyl]-L-homoserinate and 616 mg of betaine. 320 mg of expected product is obtained. The operation is carried out as in Preparation 1 (Method 2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1 g of 3-hydroxy-benzenepropanoic acid is mixed in 20 ml of methanol and 8 drops of sulphuric acid, the reaction medium is taken to reflux for 2 hours then evaporated under reduced pressure and purified by chromatography eluting with an AcOEt/Cyclohexane mixture 50/50. 1.07 g of expected product is obtained. to reflux for 2 hours then evaporated under reduced pressure purified by chromatography eluting with an AcOEt/Cyclohexane mixture 50/50

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromomethyl-4,5-diphenyloxazole (10.00 g, 3 mmol), methyl 3-(3-hydroxyphenyl)propanoate (5.73 g, 3 mmol) potassium carbonate (4.83 g, 3.5 mmol) potassium iodide (catalytic amount) and acetonetrile (150 mL) was stirred at reflux temperature. After 30 minutes, the mixture was filtered, concentrated in vacuo and the residual oil chromatographed on a column of silica gel. Elution with a mixture of hexanes and diethyl ether (3:1) furnished methyl 3-[3-((4,5-diphenyl-2-oxazolyl)methoxy]phenyl]propanoate (10.34 g, 78%) as an oil. An analytical sample was prepared by subjecting a 4 g sample to chromatography under the conditions described above to furnish pure material as an oil. at reflux temperature the mixture was filtered concentrated in vacuo the residual oil chromatographed on a column of silica gel Elution with a mixture of hexanes and diethyl ether (3:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-bromomethyl-4,5-diphenyloxazole (10.00 g, 3 mmol), methyl 3-(3-hydroxyphenyl)propanoate (5.73 g, 3 mmol) potassium carbonate (4.83 g, 3.5 mmol) potassium iodide (catalytic amount) and acetonetrile (150 mL) was stirred at reflux temperature. After 30 minutes, the mixture was filtered, concentrated in vacuo and the residual oil chromatographed on a column of silica gel. Elution with a mixture of hexanes and diethyl ether (3:1) furnished methyl 3-[3-((4,5-diphenyl-2-oxazolyl)methoxy]phenyl]propanoate (10.34 g, 78%) as an oil. An analytical sample was prepared by subjecting a 4 g sample to chromatography under the conditions described above to furnish pure material as an oil. at reflux temperature the mixture was filtered concentrated in vacuo the residual oil chromatographed on a column of silica gel Elution with a mixture of hexanes and diethyl ether (3:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20 ml of 10% hydrogen chloride-methanol was added to 1.64 g (10 mmol) of 3-hydroxycinnamic acid and the mixture was stirred at room temperature for one day. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed twice with water and dried (MgSO4). The solvent was distilled off. The residue was dissolved in 25 ml of methanol, 0.5 g of 10% palladium-carbon was added and the mixture was stirred overnight under hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1 (v/v)) to obtain 1.75 g (9.71 mmol) of methyl 3-(3-hydroxyphenyl)propionate as a colorless oily substance. Its spectroscopic data are as follows: The reaction mixture was concentrated under reduced pressure The residue was dissolved in ethyl acetate washed twice with water dried (MgSO4) The solvent was distilled off The residue was dissolved in 25 ml of methanol 0.5 g of 10% palladium-carbon was added the mixture was stirred overnight under hydrogen atmosphere The reaction mixture was filtered the filtrate was concentrated The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1 (v/v))

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20 ml of 10% hydrogen chloride-methanol was added to 1.64 g (10 mmol) of 3-hydroxycinnamic acid and the mixture was stirred at room temperature for one day. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed twice with water and dried (MgSO4). The solvent was distilled off. The residue was dissolved in 25 ml of methanol, 0.5 g of 10% palladium-carbon was added and the mixture was stirred overnight under hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1 (v/v)) to obtain 1.75 g (9.71 mmol) of methyl 3-(3-hydroxyphenyl)propionate as a colorless oily substance. Its spectroscopic data are as follows: The reaction mixture was concentrated under reduced pressure The residue was dissolved in ethyl acetate washed twice with water dried (MgSO4) The solvent was distilled off The residue was dissolved in 25 ml of methanol 0.5 g of 10% palladium-carbon was added the mixture was stirred overnight under hydrogen atmosphere The reaction mixture was filtered the filtrate was concentrated The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1 (v/v))

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Under an argon atmosphere, to a solution of methyl 3-(3-hydroxyphenyl)propanoate (131 mg), (5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methanol (200 mg) and triphenylphosphine (259 mg) in THF (3.0 mL) was added a about 2.2 M solution of diethyl azodicarboxylate in toluene (450 μL), and the mixture was stirred for 30 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (249 mg) as a colorless oil. The reaction mixture was concentrated under reduced pressure the residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (E)-methyl 3-(3-hydroxyphenyl)acrylate (15.8 g) in methanol (150 mL) was added 10% palladium-activated carbon (1.50 g) and, under a hydrogen atmosphere, the mixture was stirred at room temperature for 5 hr. The reaction mixture was filtered to remove palladium carbon, and the filtrate was evaporated under reduced pressure to give the title compound (16.0 g) as a colorless oil. This compound was used for the next step without further purification. The reaction mixture was filtered to remove palladium carbon the filtrate was evaporated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The operation is carried out as in Preparation 1 (Method 2) starting from 270 mg of the phenol prepared in Stage A, 309 mg of 1,1-dimethyl-ethyl N-[(phenylmethoxy)carbonyl]-L-homoserinate and 616 mg of betaine. 320 mg of expected product is obtained. The operation is carried out as in Preparation 1 (Method 2)