Diisobutylaluminum hydride → Benzofuran-3-ylmethanol

To a stirring solution of 650 mg (3.69 mmol) of Benzofuran-3-carboxylic acid methyl ester, prepared as in Intermediate 18, in 25 mL dichloromethane at -78° C. is added dropwise over 5 min a solution of 9.22 mL (9.22 mmol, 2.5 equiv) of a 1.0M solution of DIBAL-H in hexane. The resulting solution is allowed to slowly warm to RT over a 4 h period then quenched by careful addition of 5 mL of H2O. The reaction mixture is poured into 100 mL of EtOAc and extracted with 1N HCl (1×100 mL), dried (MgSO4), and the solvent removed in vacuo. Purification of the crude material by silica gel flash column chromatography using hexane/EtOAc 4/1 as eluent afforded 444 mg of the title compound as a pale yellow oil: 1H NMR (CDCl3, 300 MHz) δ7.66 (d, 1H), 7.60 (s, 1H), 7.49 (d, 1H), 7.29 (m, 2H), 4.82 (d, 2H), 1.70 (m, 1H); Rf =0.17 in hexane/EtOAc 5/1.

1. customthen quenched by careful addition of 5 mL of H2O
2. additionThe reaction mixture is poured into 100 mL of EtOAc
3. extractionextracted with 1N HCl (1×100 mL)
4. dry with materialdried (MgSO4)
5. customthe solvent removed in vacuo
6. customPurification of the crude material by silica gel flash column chromatography

ORD record

ord-2539028e1c3c4f6fade858e6d3e0cdd1

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05859007