3-Hydroxybenzaldehyde → HCID 22241324, compound

Temperature

0 °C

To a cooled suspension (0° C.) of 60% NaH (660 mg, 16.5 mmol) in THF (35 mL) is added dropwise a solution of 3-hydroxybenzaldehyde (1.89 g, 15 mmol) in THF (15 mL) and the resulting mixture stirred for 20 min. To the mixture is added 2-methoxyethoxymethyl chloride (1.88 mL, 16.5 mmol) and DMPU (5 mL), the cold bath removed and stirred for 1 hr. The reaction mixture is cooled to 0° C. then slowly added 2M NaBH4 (in triglyme) (3.75 mL, 7.5 mmol) and let stir for 1 hr. Slowly quenched with 2N HCl soln (3.9 mL) and diluted reaction mixture with ether. The organic layer is washed with brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 60% ethyl acetate in hexanes) to give the title compound as a pale yellow oil. MS (EI) 212 (M)+.

1. customthe cold bath removed
2. stirringstirred for 1 hr
3. customSlowly quenched with 2N HCl soln (3.9 mL)
4. additiondiluted
5. customreaction mixture with ether
6. washThe organic layer is washed with brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated
9. customThe residue is purified by flash chromatography (silica, 60% ethyl acetate in hexanes)

ORD record

ord-8db9fa62e91c44639ce1682153cf6295

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07005440B1