1.1
Reagents:
Sodium bis(trimethylsilyl)amide
Solvents:
Tetrahydrofuran
;
30 min, cooled; -78 °C
1.2
Solvents:
Tetrahydrofuran
;
-78 °C; 1.5 h, -78 °C; 1 h, -78 °C → rt
1.3
Reagents:
Acetic acid
;
30 min, pH 7, rt
2.1
Reagents:
Hydrogen
Catalysts:
Palladium
Solvents:
Methanol
;
1 h, 1 atm, 25 °C
2.2
Reagents:
Iodine
,
Silver sulfate
Solvents:
Methanol
;
3 h, 25 °C
3.1
Reagents:
Butyllithium
Solvents:
Tetrahydrofuran
,
Hexane
;
-78 °C; 30 min, -78 °C
3.2
Reagents:
Trimethyl borate
;
3 h, -78 °C
3.3
Reagents:
Ammonium chloride
Solvents:
Water
;
-78 °C → rt