Dichloromethane → HCID 131730732, compound

Temperature

-100 °C

A mixture of THF (2 L) and DCM (55.3 g, 0.651 mol) was cooled to −100° C. n-BuLi (260.7 mL, 2.5 M in n-hexane, 0.651 mol) was added dropwise into the reaction mixture maintaining at −100° C. Pinacol 2-methylpropane-1-boronate ([2]; 100 g, 0.543 mol) was added into the reaction mixture. The resulting mixture was keep at −100° C. for one hour. A solution of ZnCl2 (136.3 g, 1.0 mol) in THF (500 mL) was added dropwise to the reaction over a period of 60 minutes. The resulting mixture was keep at −100° C. for one hour, the reaction mixture was warmed up to room temperature and keep at room temperature overnight. The reaction was diluted with MTBE (750 mL) and was washed twice with saturated NH4Cl (2 L each). The organic layer was dried overnight over MgSO4 before filtering and evaporating. n-Heptane (250 mL) was added into the mixture and was filtered and evaporated providing the product as an oil (119.5 g, 0.514 mol). 1H NMR (300 MHz, CDCl3) δ 3.48 (dd, J=9.8, 6.1 Hz, 1H), 1.93-1.71 (m, 2H), 1.61 (td, J=8.1, 4.0 Hz, 1H), 1.33-1.24 (m, 12H), 0.95-0.87 (m, 6H); 13C NMR (75 MHz, CDCl3) δ 84.5, 42.8, 25.8, 24.8, 23.1, 21.5.

1. additionwas added dropwise into the reaction mixture
2. waitThe resulting mixture was keep at −100° C. for one hour
3. temperaturethe reaction mixture was warmed up to room temperature
4. waitkeep at room temperature overnight
5. washwas washed twice with saturated NH4Cl (2 L each)
6. dry with materialThe organic layer was dried overnight over MgSO4
7. filtrationbefore filtering
8. customevaporating
9. additionn-Heptane (250 mL) was added into the mixture
10. filtrationwas filtered
11. customevaporated

ORD record

ord-8f26f90babb140aebbedec4cb269612b

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08497374B2