Boron trifluoride etherate → HCID 56763784, compound

To solution of 3-furonitrile (5 g, 53.71 mmol, 1.0 eq) in dry THF at r.t. under an argon atmosphere was added slowly titanium isopropoxide (18.9 ml, 64.4 mmol, 1.2 eq). The reaction mixture was stirred for 15 min. A solution of 1.0 Methyl magnesium bromide in THF (129 ml, 128 mmol, 2.4 eq) was added via syringe slowly to the mixture at 0° C. After addition, the reaction mixture was stirred at r.t. for 2 hour. BF3.Et2O (10.4 ml) was then added slowly to the mixture at 0° C. After completion of the addition, the reaction mixture was stirred at r.t. for 30 min. 10% NaOH solution was added slowly till the reaction mixture becomes basic and then 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 (38%). 1H NMR (400 MHz, CDCl3): δ 7.32 (m, 2H), 6.10 (s, 1H), 0.98-0.95 (m, 2H), 0.83-0.78 (m, 2H). LCMS: (ES+) m/z=123.7 (M)+

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

ORD record

ord-2da3d0d627d84cd4ad53d7be82d4cd93

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148382B2