Methanol → HCID 13611238, compound

Participants

Reaction Steps

A solution of (S)-2-methoxymethoxybutanedioic acid, bis methoxymethyl ester (10 g, 37.5 mmol) in dry tetrahydrofuran (10 ml) under dry nitrogen was treated with borane dimethylsulphide (8.3 ml, 83 mmol). The solution was heated between 60° C. and 80° C. over a period of 5.5 hours and then cooled in ice and treated dropwise with methanol (50 ml). After effervescence had ceased the solution was stirred at room temperature for 18 hours and the solvent removed under vacuum. The residue was evaporated to dryness with methanol (2×50 ml) and the residue chromatographed on silica, eluting with chloroform-methanol 5:1 to give (S)-1,4-dihydroxy-2-(methoxymethoxy)butane (3.9 g, 69%); IR: υmax (film) 3400, 2940, 2890, 2820, 1470, 1440, 1410, 1380, 1300, 1210, 1150, 1100, 1030, 920 cm-1 ; 1H NMR: δH (CDCl3) 1.78 (2H, m, CH2), 2.96 (2H, s, D2O exchangeable OH's), 3.44 (3H, s, OCH3), 3.5-3.85 (5H, m, CH plus 2×CH2 's), 4.72 (1H, d, J=7 Hz, CH of CH2), 4.77 (1H, d, J=7 Hz, CH of CH2).

Provenance & Evidence