Multi-step reaction with 21 steps
1: 1.) acetone, MeOH, water; 2.) water, HCl, pH=3, EtOH
2: NaNO2 / H2O; H2SO4 / 0 - 25 °C
3: diethyl ether
4: p-TsOH / diethyl ether / Ambient temperature
5: LAH / diethyl ether
6: p-TsOH / methanol / Ambient temperature
7: p-TsOH / Ambient temperature
8: NaCH2SOMe / dimethylsulfoxide / 5 h / Ambient temperature
9: aq. HCl; methanol; H2O / 6.5 h / 60 °C
10: 92 percent / pyridine / 0 - 5 °C
11: 66 percent / KOH / methanol / 0.58 h / 0 - 17 °C
12: 82 percent / CuI / diethyl ether / -55 - -20 °C
13: 98 percent / p-TsOH / diethyl ether / Ambient temperature
14: 88 percent / H2 / Pd-C (5percent) / ethanol
15: 2.) p-TsOH, dihydropyran / 1.) C5H5N, 8 h; 2.) ether, room temp.
16: K2CO3, NaI / acetone / 120 h / Ambient temperature
17: 98 percent / p-TsOH / methanol / Ambient temperature
18: TsOH-C5H5N (PPTS) / Ambient temperature
19: LDA / diethyl ether / -115 - -20 °C
20: 2.) aq. HCl / 1.) 16 h, reflux; 2.) n-pentane, 35 min., room temp.
21: pyridine / Ambient temperature
With
3,4-dihydro-2H-pyran; hydrogenchloride; potassium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; dimsylsodium; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; toluene-4-sulfonic acid; sodium iodide; lithium diisopropyl amide; sodium nitrite;
palladium on activated charcoal;
In
pyridine; hydrogenchloride; methanol; diethyl ether; ethanol; sulfuric acid; water; dimethyl sulfoxide; acetone;
DOI:10.1016/0040-4020(82)80081-1