1.1
Reagents:
Diisopropylethylamine
Solvents:
Dichloromethane
;
10 min, rt
1.2
rt; 12 h, rt
1.3
Solvents:
Water
;
rt
2.1
Reagents:
Sodium borohydride
Solvents:
Methanol
;
30 min, rt
2.2
Reagents:
Hydrochloric acid
Solvents:
Water
;
rt
3.1
Reagents:
Carbon tetrabromide
,
Triphenylphosphine
Solvents:
Diethyl ether
;
rt
4.1
Solvents:
Toluene
;
12 h, reflux
5.1
Reagents:
Butyllithium
Solvents:
Tetrahydrofuran
,
Hexane
;
-78 °C; 30 min, -78 °C; -78 °C → rt; 1 h, rt; rt → -78 °C
5.2
Solvents:
Tetrahydrofuran
;
1 h, -78 °C; 18 h, rt
5.3
Solvents:
Water
;
rt
6.1
Reagents:
Tetrabutylammonium fluoride
Solvents:
Tetrahydrofuran
;
1.5 h, 0 °C
6.2
Reagents:
Hydrochloric acid
Solvents:
Water
;
0 °C
7.1
Reagents:
Potassium hydroxide
Solvents:
Ethanol
;
40 min, rt
7.2
Solvents:
Water
;
rt