Cyclohexanecarboxaldehyde → 2-(4-Bromo-2,6-dimethyl-phenyl)-5-(cyclohexyl-hydroxy-methyl)-3-methoxy-cyclopent-2-enone

Temperature

-78 °C

To a solution of 2-(4-bromo-2,6-dimethyl-phenyl)-3-methoxy-cyclopent-2-enone (1 g, 3.4 mmol) in 10 ml of dry tetrahydrofuran under nitrogen atmosphere at −78° C. LiHMDS (4.42 ml, 4.42 mmol) is added slowly and it is stirred at −78° C. for 40 minutes. A solution of cyclohexyl carboxaldehyde (761 mg, 6.8 mmol) in dry tetrahydrofuran (10 ml) is added to the reaction mixture at −78° C. The reaction mixture is stirred at this temperature for 2 hours and then at room temperature for 3 hours. The reaction mixture is quenched with water (50 ml) and the aqueous layer is extracted with ethyl acetate (3*100 ml). The combined organic layers are dried with sodium sulfate and concentrated under vacuum to obtain crude product which is directly taken to the next step without further purification.

1. customat −78° C
2. stirringThe reaction mixture is stirred at this temperature for 2 hours
3. waitat room temperature for 3 hours
4. customThe reaction mixture is quenched with water (50 ml)
5. extractionthe aqueous layer is extracted with ethyl acetate (3*100 ml)
6. dry with materialThe combined organic layers are dried with sodium sulfate
7. concentrationconcentrated under vacuum
8. customto obtain crude product which
9. customis directly taken to the next step without further purification

ORD record

ord-2d4d495a604a4eb4919a799b10d5ca78

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791303B2