Isobutyryl chloride → 1-(2,6-Bis{[(methyloxy)methyl]oxy}phenyl)-2-methyl-1-propanone

1,3-bis{[(methyloxy)methyl]oxy}benzene (Intermediate 35, 2.2 g) was dissolved under nitrogen in THF (8.0 mL) and a solution of BuLi (8.32 mL of a 1.6 M solution in hexane, 13.3 mmol) was added. After stirring at room temperature for 1 hour, cooling down to −78° C., 2-methylpropanoyl chloride (4.65 ml, 44.4 mmol) was added and the reaction mixture was stirred at that temperature for 1 hour. After quenching with water, the reaction mixture was extracted with ethyl acetate. The gathered organic layers were dried over sodium sulphate, filtered and evaporated. The residue obtained was then charged on a silica gel column (Biotage SP1 system) and eluted with Cyclohexane/EtOAc (from all 10/0 to 9/1, then 9/1, then from 9/1 to 8/2, then 8/2) to afford the title compound (825 mg).

1. temperaturecooling down to −78° C.
2. stirringthe reaction mixture was stirred at that temperature for 1 hour
3. customAfter quenching with water
4. extractionthe reaction mixture was extracted with ethyl acetate
5. dry with materialThe gathered organic layers were dried over sodium sulphate
6. filtrationfiltered
7. customevaporated
8. customThe residue obtained
9. additionwas then charged on a silica gel column (Biotage SP1 system)
10. washeluted with Cyclohexane/EtOAc (from all 10/0 to 9/1

ORD record

ord-a94f2a77d8834f1bbb28062d7d3a780c

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09346790B2