1.1
Catalysts:
Pyridinium p-toluenesulfonate
Solvents:
Dichloromethane
;
4 h, rt
1.2
Reagents:
Sodium bicarbonate
Solvents:
Water
2.1
Reagents:
Tetrabutylammonium fluoride
Solvents:
Tetrahydrofuran
;
1 h, rt
2.2
Solvents:
Water
;
pH 7
3.1
Reagents:
Potassium tert-butoxide
Catalysts:
Bis(1,5-cyclooctadiene)nickel
,
Tricyclohexylphosphine
Solvents:
Toluene
;
2 h, reflux; reflux → rt
3.2
Reagents:
Ammonium chloride
Solvents:
Water
4.1
Reagents:
Aluminum chloride
,
Lithium aluminum hydride
Solvents:
Diethyl ether
;
30 min, 0 °C
4.2
Solvents:
Dichloromethane
,
Toluene
;
20 min, 0 °C
4.3
Reagents:
Triethylamine
Solvents:
Water
5.1
Reagents:
Sodium hydride
,
15-Crown-5
Solvents:
Toluene
,
1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
;
2 h, 80 °C
5.2
Reagents:
Water
6.1
Reagents:
Hydrogen
Catalysts:
Palladium
Solvents:
tert-Butanol
,
Water
;
15 h, rt
7.1
Reagents:
Dess-Martin periodinane
Solvents:
Dichloromethane
;
15 min, rt
7.2
Reagents:
Sodium bicarbonate
,
Sodium thiosulfate
Solvents:
Water
7.3
Reagents:
Hydrochloric acid
Solvents:
Methanol
;
1.5 h, 50 °C
7.4
Reagents:
Sodium bicarbonate
Solvents:
Water
8.1
Reagents:
Pyridine
,
Thionyl chloride
;
30 min, 0 °C
8.2
Reagents:
Hydrochloric acid
Solvents:
Water
;
0 °C