Cyclohexanecarboxaldehyde → Cyclohexyl(2-methyl-1-benzothiophen-3-yl)methanol

3-Bromo-2-methyl-1-benzothiophene (2.00 g) synthesized above was dissolved in tetrahydrofuran (40 mL), 1.6M n-butyllithium hexane solution (6.63 mL) was added dropwise at −78° C. The mixture was stirred under a nitrogen atmosphere for 10 min, cyclohexanecarbaldehyde (2.50 mL) was added, and the mixture was stirred −78° C. for 30 min and at room temperature for 30 min. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:17, volume ratio) to give the title object compound (1.95 g, 85%) as a yellow oil.

1. stirringthe mixture was stirred −78° C. for 30 min and at room temperature for 30 min
2. customto quench
3. customthe reaction
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with saturated brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:17, volume ratio)

ORD record

ord-debd51f70c064c81bdf74446b278c1c3

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436043B2