Dimethylformamide → 3-Methoxy-2-(methoxymethyl)propan-1-ol

Sodium hydride (60% dispersion in oil) (2.93 g, 73.2 mmol) was added to an ice-cooled solution of 2-hydroxymethyl-propane-1,3-diol (M. R. Harnden et al. J. Med. Chem. 1990, 33, 187) (3.53 g, 33.3 mmol) in DMF (100 ml) and the mixture was stirred at room temperature for 40 min. The reaction mixture was cooled with ice and iodomethane (4.56 ml, 73.2 mmol) was added, the stirring was continued allowing the mixture to reach room temperature over 24 h. The mixture was poured into ethyl acetate (300 ml) and washed with brine (150 ml). The organic phase was dried (MgSO4), and the solvent was evaporated. The crude product was purified by flash column chromatography (silica, ethyl acetate) to afford colourless oil. 1H NMR (300 MHz, CDCl3) 3.72 (2H, d), 3.47 (2H, d), 3.45 (2H, d), 3.32 (6H, s), 2.07(1H, m).

1. additionwas added
2. waitto reach room temperature over 24 h
3. washwashed with brine (150 ml)
4. dry with materialThe organic phase was dried (MgSO4)
5. customthe solvent was evaporated
6. customThe crude product was purified by flash column chromatography (silica, ethyl acetate)
7. customto afford colourless oil

ORD record

ord-a6674fc277384ed1ab1f050c95528039

Source dataset

uspto-grants-2002_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06479531B1