Multi-step reaction with 14 steps
1: dimethyl sulphoxide, oxalyl chloride
2: 58 percent / triethylamine, 3-(2-ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide / thiazolium salt / dioxane / 56 h / 80 °C
3: 70 percent / toluene-p-sulphonic acid / benzene / 16 h / Heating
4: 1.) ozone, 2.) sodium borohydride / 1.) methanol, CH2Cl2, -70 deg C, 2 h, 2.) -70 deg C, 1 h, room temperature, 2 h
5: 81 percent / tributylphosphine / tetrahydrofuran / 65 h
6: 87 percent / 1M aq. NaOH, hydrogen peroxide / tetrahydrofuran / 1.) 0 deg C, 5 min 2.) room temperature, 16 h
7: 1.) ozone, 2.) dimethyl sulphide / 1.) methanol, -72 deg C, 35 min, 2.) room temperature, 2 h
8: 1.) butyl-lithium, 2.) hexamethylphosphoric triamide / 1.) hexane, THF, -70 deg C, 1 h, 2.) room temperature, 3 h
9: 4.05 g / sodium hydroxide / ethanol; H2O / 4 h / Ambient temperature
10: 98 percent / tetrahydrofuran / 16 h / Ambient temperature
11: 1.) lithium hexamethyldisilazide, 2.) lithium hexamethyldisilazide / 1.) THF, -72 deg C, 6 h, room temperature, 1 h, 2.) -72 deg C, 4 h
12: aq. hydrogen peroxide, m-chloroperoxybenzoic acid / CHCl3 / 1.) -50 deg C, 15 min, 2.) 0 deg C, 10 min
13: 58 percent / toluene / 16 h / 80 °C
14: 84 percent / sodium hydroxide / methanol; H2O / 2.5 h
With
N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; dimethylsulfide; tributylphosphine; dihydrogen peroxide; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 3-(2-Ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazoliumbromid; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane;
thiazolium salt;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; chloroform; water; toluene; benzene;
