1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 2) -78 deg C to r.t., overnight 2: 85 percent / N-bromosuccinimide / acetone; H2O / 0.5 h / 5 deg C to r.t. View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -20 °C 1.2: -20 °C 2.1: NiII chloride hexahydrate; sodium tetrahydroborate / tetrahydrofuran; methanol / 0 - 30 °C 3.1: trifluoroacetic acid / methanol / 0 °C 4.1: dipyridinium dichromate / N,N-dimethyl-formamide / 15 h / 30 °C View Scheme

Mg(HSO4)2 in acetonitrile T=20°C; 0.0666667 h; chemoselective reaction;

acetyl chloride in methanol 6 h; Heating;

methanol; acetyl chloride T=20°C; 2 h;

in methanol 2 h; Heating;