Boron trifluoride etherate → 1-(furan-2-yl)cyclopropanaMine

To a solution of 2-furonitrile (5 g, 53.71 mmol, 1.0 eq) in dry THF under an argon atmosphere was added slowly titanium isopropoxide (18.9 ml, 64.4 mmol, 1.2 eq) at r.t. The reaction mixture was stirred for 15 min. A 1M solution of EtMgBr in THF (129 ml, 129 mmol, 2.4 eq) was added slowly via syringe to the mixture at 0° C. After addition, the reaction mixture was allowed to warm to r.t. and stirred at r.t. for 2 hour. BF3.Et2O (10.4 ml) was then added slowly to the mixture at 0° C. After the completion of addition, the reaction mixture was stirred at r.t. for 30 min. The reaction mixture was added with ice, and then with 10% NaOH solution slowly till the reaction mixture becomes basic. The mixture was extracted with EtOAc. The organic was washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by silica gel (60-120) column chromatography using 35% EtOAc/Pet ether as eluent. Yield: 2.5 g (crude).

1. additionAfter addition
2. stirringstirred at r.t. for 2 hour
3. additionAfter the completion of addition
4. stirringthe reaction mixture was stirred at r.t. for 30 min
5. additionThe reaction mixture was added with ice
6. extractionThe mixture was extracted with EtOAc
7. washThe organic was washed with brine
8. dry with materialdried over Na2SO4
9. concentrationconcentrated
10. customThe crude product was purified by silica gel (60-120) column chromatography

ORD record

ord-912cc34b7fbb4c26a4c4d912313e46a1

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309558B2