2H-Pyran-4-carboxylic acid, 4-(4-bromophenyl)tetrahydro-, methyl ester synthesis
- Product Name:2H-Pyran-4-carboxylic acid, 4-(4-bromophenyl)tetrahydro-, methyl ester
- CAS Number:894399-90-7
- Molecular formula:C13H15BrO3
- Molecular Weight:299.16
Yield:894399-90-7 24%
Reaction Conditions:
Stage #1: (4-bromo-phenyl)-acetic acid methyl esterwith sodium hydride;15-crown-5 in N,N-dimethyl-formamide at 20; for 0.666667 h;
Stage #2: 3-oxa-1,5-dichloropentanewith sodium iodide in N,N-dimethyl-formamide at 20; for 10 h;
Steps:
9
To a stirred solution of (4-bromophenyl)-acetic acid methylester (12.52 g, 54.6 mmol) and 15-crown-5 (1.2 g, 5.46 mmol) in DMF (100 ml) at room temperature was added NaH (60 %)(4.74 g, 119 mmol) portionwise. After stirring at room temperature for 40 minutes, NaI (8.14 g, 54.6 mmol) and 2-chloroethyl ether (13.76 g, 96.2 mmol) were added. The reaction mixture was stirred at room temperature for 10 hours, after which the solvent was evaporated in vacuo. The residue was treated with a mixture of EtOAc and toluene (1:1) and washed with a solution of 0.5 N HCl. The aqueous layer was further extracted with more EtOAc/toluene (1 :1) and the combined organic extracts were washed with water, then with an aqueous saturated solution of NaHCO3 and finally with brine. The combined organic extracts were dried (Na2SO4) and the solvent
References:
WO2009/33703,2009,A1 Location in patent:Page/Page column 28-29
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