1,2-Dichloroethane → Benzenepropanoyl chloride

A mixture of 2-amino-2-methyl-1-propanol (4 ml, 42 mmol), CH2Cl2 (200 mL), 4-acetyl benzoic acid (1, 6.9 g, 42 mmol), EDC (1-(3-dimethylaminopropyl)-3-eythylcarbodiimide HCl, 12.1 g, 63 mmol), HOBT (N-hydroxybenzotriazole H2O, 6.4 g, 42 mmol), and Hunig's base (diisopropylethylamime, 22 mL, 126 mmol) was stirred at room temperature for 18 hours. Upon completion (TLC, LC/MS) the reaction mixture was concentrated, and the resulting residue was diluted with EtOAc (50 mL) and washed with NaHCO3 (2×40 mL) and brine (40 mL). The organic layer was dried (MgSO4), filtered, and the filtrate was concentrated. The crude material was purified by flash column chromatography (4:1:1 hexanes:EtOAc:CH2Cl2; 1:1:1 hexanes:EtOAc:CH2Cl2; 1:1 EtOAc:CH2Cl2) to remove bisacylated material. Alcohol 2 was obtained in 54% yield (5.36 g).

1. concentrationUpon completion (TLC, LC/MS) the reaction mixture was concentrated
2. additionthe resulting residue was diluted with EtOAc (50 mL)
3. washwashed with NaHCO3 (2×40 mL) and brine (40 mL)
4. dry with materialThe organic layer was dried (MgSO4)
5. filtrationfiltered
6. concentrationthe filtrate was concentrated
7. customThe crude material was purified by flash column chromatography (4:1:1 hexanes:EtOAc:CH2Cl2; 1:1:1 hexanes:EtOAc:CH2Cl2; 1:1 EtOAc:CH2Cl2)
8. customto remove bisacylated material

ORD record

ord-f3672bea3bc94628b99323a1c27e4997

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329928B2