Triethyl phosphonoacetate → Ethyl(2E)-2-[(3R,3aS,6aR)-3-[tert-butyl(dimethyl)silyl]oxy-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-ylidene]acetate

A 20 mL sample vial was charged (3R,3aS,6aS)-3-[tert-butyl(dimethyl)silyl]oxy-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-one (400 mg, 1.548 mmol), ethyl 2-(diethoxyphosphoryl)acetate (521 mg, 2.322 mmol) and THF (5 ml). The vial was flushed with nitrogen and cooled in an ice bath. To the mixture was then added slowly 60% sodium hydride (93 mg, 2.3 mmol) and the resulting reaction mixture was stirred at room temperature for 6 h. The reaction was partitioned between water (10 mL) and ethyl acetate (20 mL). The aqueous layer was extracted with ethyl acetate (3×10 mL). The combined organic phases were dried over MgSO4, filtered and concentrated. The resulting residue was then purified by MPLC (40 g silica gel, 0 to 20% ethyl acetate in hexanes) to afford the desired product as a mixture of E/Z isomers. LC-MS: calculated for C16H28O5Si, [M+H]+Calc: 328.17. Found: 329.2, Rt=2.24 and 2.31 min (E and Z mix, 4 min run).

1. customThe vial was flushed with nitrogen
2. temperaturecooled in an ice bath
3. customthe resulting reaction mixture
4. customThe reaction was partitioned between water (10 mL) and ethyl acetate (20 mL)
5. extractionThe aqueous layer was extracted with ethyl acetate (3×10 mL)
6. dry with materialThe combined organic phases were dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe resulting residue was then purified by MPLC (40 g silica gel, 0 to 20% ethyl acetate in hexanes)

ORD record

ord-be9720a9f7ad47ceaf6458bb338a4a04

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290517B2