Water → HCID 22592416, compound

Temperature

0 °C

To a stirred suspension of sodium hydride (247 mg, 6.16 mmol) in dry THF (6 ml) at 0° C. under nitrogen was added a solution of diethylcyanomethyl phosphonate (0.98 ml, 6.16 mmol) in 2 ml THF and the whole stirred at 0° C. for 1 h. 5-Acetyl-2,3-dihydro[b]benzofuran (Aldrich) (1 g, 6.16 mmol) in THF (2 ml) was added dropwise and the whole stirred at room temperature for 16 h. Water (20 ml) and EtOAc (20 ml) were added, the organic layer separated, and the aqueous layer extracted with EtOAc (2×20 ml). The combined organics were dried over MgSO4, filtered and evaporated to afford a pale brown oil which solidified on standing. This solid was purified by column chromatography using 20-30% EtOAc in pentane as eluant to give the title product (789 mg, 69%); 1HNMR (400 MHz, CDCl3) δ: 2.4 (s, 3H), 3.2 (t, 2H), 4.6 (t, 2H), 5.5 (s, 1H), 6.7 (d, 1H), 7.2 (d, 1H), 7.3 (s, 1H); LRMS: M+NH4 203 (ES+).

1. stirringthe whole stirred at room temperature for 16 h
2. customthe organic layer separated
3. extractionthe aqueous layer extracted with EtOAc (2×20 ml)
4. dry with materialThe combined organics were dried over MgSO4
5. filtrationfiltered
6. customevaporated
7. customto afford a pale brown oil which
8. customThis solid was purified by column chromatography

ORD record

ord-523270742c04421d866cefd08800786d

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06660756B2