Dichloromethane → 4-(Benzenesulfonyl)-3-methylbutan-1-ol

Temperature

-78 °C

A solution of methanesulphonylbenzene (2.17 g, 13.9 mmol) in tetrahydrofuran (10 ml) was cooled to −78° C. and treated with butyllithium (1.6M in hexanes, 8.7 ml, 13.9 mmol) followed by 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (1.68 ml, 13.9 mmol). The reaction was stirred at −78° C. for 15 minutes then methyl crotonate (7.36 ml, 69.5 mmol) added. The reaction was allowed to warm to room temperature and quenched with water. The mixture was extracted with ethyl acetate and the combined organic layers dried (MgSO4)and concentrated in vacuo. The residue was dissolved in dichloromethane (10 ml) and cooled to −5° C. A solution of diisobutylaluminium hydride in dichloromethane (1M, 27.8 ml, 27.8 mmol) was added and the reaction allowed to warm to room temperature. The mixture was diluted with aqueous ammonium carbonate solution and extracted with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated in vacuo. A portion of the residue was purified by preparative thin layer chromatography, eluting with 5% methanol/dichloromethane, to give the title compound.

1. temperatureto warm to room temperature
2. customquenched with water
3. extractionThe mixture was extracted with ethyl acetate
4. concentrationthe combined organic layers dried (MgSO4)and concentrated in vacuo
5. dissolutionThe residue was dissolved in dichloromethane (10 ml)
6. temperaturecooled to −5° C
7. temperatureto warm to room temperature
8. extractionextracted with ethyl acetate
9. dry with materialThe combined organic layers were dried (MgSO4)
10. concentrationconcentrated in vacuo
11. customA portion of the residue was purified by preparative thin layer chromatography
12. washeluting with 5% methanol/dichloromethane

ORD record

ord-a4dccfdb4cee41858730331ac136ffa0

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07101892B2