Sodium Iodide → HCID 118060815, compound

The solution of ethyl 3-methylenecyclobutanecarboxylate (1 g, 7.13 mmol), NaI (0.214 g, 1.427 mmol) and TMSCF3 (2.54 g, 17.83 mmol) in THF (10 mL) was stirred at 65° C. for 2 h. The reaction mixture was quenched with a 10% aq. solution of NaHCO3 and the aqueous layer was extracted with diethyl ether (3×10 mL). The combined organic layer was washed with a 10% aq. solution of NaHCO3, followed by brine, then dried over Na2SO4, filtered and the filtrate concentrated. The crude was purified by silica gel chromatography (12 g REDISEP® column, eluting with 20% EtOAc in hexane). Fractions containing the product were combined and evaporated to afford Intermediate 320A as a pale yellow liquid (1 g, 73%, mixture of cis and trans isomers). 1H NMR (400 MHz, chloroform-d) δ ppm 4.13-4.24 (m, 2H) 2.56-2.65 (m, 1H), 2.01-2.06 (m, 2H), 1.91-1.98 (m, 2H) 1.16-1.45 (m, 5H).

1. customThe reaction mixture was quenched with a 10% aq. solution of NaHCO3
2. extractionthe aqueous layer was extracted with diethyl ether (3×10 mL)
3. washThe combined organic layer was washed with a 10% aq. solution of NaHCO3
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationthe filtrate concentrated
7. customThe crude was purified by silica gel chromatography (12 g REDISEP® column, eluting with 20% EtOAc in hexane)
8. additionFractions containing the product
9. customevaporated

ORD record

ord-d501a5f423ad4987b58c8733bcd8aaa1

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273058B2