Trimethylsilyldiazomethane → [5-(4-Chlorophenyl)-2-methylfuran-3-yl]methanol

To a solution of 5-(4-chlorophenyl)-2-methylfuran-3-carboxylic acid (0.104 g, 0.44 mmol) in THF (2 mL) and MeOH (2 mL) was added TMSCHN2 (2.0 M in Et2O, 0.250 mL). The reaction mixture was stirred for 18 hours at which time it was concentrated in vacuo. The residue was dissolved in 1 ml of THF at 0° C., and a solution of LAH (1.0 M in THF, 0.8 mL) was added. After addition, the reaction was stirred at room temperature for 2 hours, and then water (0.24 mL), 15% aqueous NaOH (0.24 mL), and water (0.72 mL) were added sequentially to the reaction. After 30 minutes, the reaction mixture was filtered through celite, and the filtrate was concentrated to give 53.1 (0.056 g). 1H NMR (400 MHz, CDCl3) δ ppm 7.53-7.63 (m, 2 H), 7.31-7.40 (m, 2 H), 6.64 (s, 1 H), 4.52 (s, 2 H), 2.37 (s, 3 H).

1. concentrationwas concentrated in vacuo
2. dissolutionThe residue was dissolved in 1 ml of THF at 0° C.
3. additiona solution of LAH (1.0 M in THF, 0.8 mL) was added
4. additionAfter addition
5. stirringthe reaction was stirred at room temperature for 2 hours
6. additionwater (0.24 mL), 15% aqueous NaOH (0.24 mL), and water (0.72 mL) were added sequentially to the reaction
7. waitAfter 30 minutes
8. filtrationthe reaction mixture was filtered through celite
9. concentrationthe filtrate was concentrated

ORD record

ord-9334d8ca85a8447c9bdf6052fedf072f

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003648B2