hydrogenchloride; acetic acid

1: 1.) NaH / 1.) dimethylacetamide, 1-1.5 h, 40 deg C; 2.) dimethylacetamide, 5 h, 90 deg C 2: KOH / methanol / 20 h / Ambient temperature 3: SOCl2 / 16 h / Ambient temperature 4: LiAlH(O-tBu)3 / bis-(2-methoxy-ethyl) ether / 0.5 h / -60 °C 5: 1.) Na2S2O5; 2.) KCN / 1.) H2O, EtOH, 16 h, 55 deg C; 2.) H2O, EtOH, 7 h, reflux 6: LiAlH4 / diethyl ether; tetrahydrofuran / also with BH3; 1.) 16 h, RT; 2.) 1 h, 40 deg C 7: Et3N / CH2Cl2 / 0.5 h / -5 °C View Scheme

in diethyl ether T=-60°C;

phosphate buffer in ethanol T=30°C; 12 h; Anr4 cell line; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Candida cylindracea lipase in phosphate buffer; ethyl acetate T=20°C; 48 h; Product distribution; Further Variations:Reagents;

1: NaOAc / ethanol / 2.33 h / Heating 2: NaH / methanol / 2 h / Heating View Scheme

sodium acetate in ethanol 2.33333 h; Heating;

1: 175 °C 2: aq. HCl / 160 °C 3: 200 °C View Scheme

scandium tris(trifluoromethanesulfonate) T=64°C; 12 h;

lithium aluminium tetrahydride; diethyl ether