Stannous chloride dihydrate → HCID 44139029, compound

Tin(ii) chloride dihydrate (11.5 g, 51 mmol) was added to a stirred solution of tert-butyl (E,E)-4-methyl-5-(4-nitrophenyl)penta-2,4-dienoate (3.67 g, 12.7 mmol) in methanol (75 ml). The mixture was stirred and heated at reflux and the reaction monitored by HPLC. After 70 min, 4% starting material remained and there were two new products comprising 90 and 6% respectively. The cool mixture was concentrated in vacuo, water (75 ml) was added to the residue and then 2N NaOH solution until at pH 11. Ethyl acetate (150 ml) was added and the mixture filtered through Celite. The EtOAc layer was washed with 5% NaCl solution, dried over MgSO4 and concentrated in vacuo. The residual oil was stirred in diisopropyl ether (20 ml) for 10 min, insoluble by-products removed by filtration and the filtrate concentrated in vacuo to give 2.8 g (86%) of a yellow solid, mp 99-101° C.

1. temperatureheated
2. temperatureat reflux
3. concentrationThe cool mixture was concentrated in vacuo, water (75 ml)
4. additionwas added to the residue
5. additionEthyl acetate (150 ml) was added
6. filtrationthe mixture filtered through Celite
7. washThe EtOAc layer was washed with 5% NaCl solution
8. dry with materialdried over MgSO4
9. concentrationconcentrated in vacuo
10. stirringThe residual oil was stirred in diisopropyl ether (20 ml) for 10 min
11. custominsoluble by-products removed by filtration
12. concentrationthe filtrate concentrated in vacuo

ORD record

ord-30dd2729b5184b9092edfa50bca4f0e5

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08236985B2