Boron trifluoride etherate → 179802-16-5

Into a dried 3L three neck-round bottom flask with a stirrer bar, nitrogen-inlet, thermocouple and a 1L-addition funnel was charged 1227.2 g (11.56 mol) of trimethyl-orthoformate, which was cooled to −5° C. to −3° C. while agitating. The reaction mixture was charged with 3.855 g BF3.Et2O (21 mmol) while agitating under nitrogen. The addition funnel was then charged with a mixture of 315.41 g 2,3-dihydrofurane (4.5 mol) and 434.64 g trimethylorthoformate (4.1 mol) and this mixture was added to the reaction mixture over a period of 160-180 minutes while maintaining the temperature at −5° to −3° C. After the addition was complete, the reaction was quenched with 3.24 g NaOH (81 mmol) in 12.96 g MeOH and left 16 h at 15° C. The reaction mixture was filtered and distilled first under atmospheric pressure, then under reduced pressure. The intermediate product obtained boils at 79-85° C. at 6.8-6.9 mmHg and is a mixture of diastereomers.

1. dry with materialInto a dried 3L three neck-round bottom flask with a stirrer bar, nitrogen-inlet
2. temperaturewas cooled to −5° C. to −3° C.
3. stirringwhile agitating under nitrogen
4. additionthis mixture was added to the reaction mixture over a period of 160-180 minutes
5. temperaturewhile maintaining the temperature at −5° to −3° C
6. additionAfter the addition
7. filtrationThe reaction mixture was filtered
8. distillationdistilled first under atmospheric pressure
9. customThe intermediate product obtained boils at 79-85° C. at 6.8-6.9 mmHg
10. additiona mixture of diastereomers

ORD record

ord-386ba0823761400a97a9e7d61e035457

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07282583B2